Boceprevir InterMediates

Product Name: Boceprevir InterMediates
CAS No.: 565456-77-1
Chemical Name: Boceprevir InterMediates
Synonyms: Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;(1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;(1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride;tert-butyl ((S)-1-cyano-2-((S)-2-oxopyrrolidin-3-yl)ethyl)carbamate;(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;Boceprevir INT 1;Paxlovid Impurity 2
CBNumber: CB12466508
Molecular Formula: C9H16ClNO2
Formula Weight: 205.68
MOL File: 565456-77-1.mol

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Boceprevir InterMediates Property

storage temp.: Inert atmosphere,Room Temperature
form: solid
color: Pale yellow
InChI: InChI=1/C9H15NO2.ClH/c1-9(2)5-4-10-7(6(5)9)8(11)12-3;/h5-7,10H,4H2,1-3H3;1H/t5-,6-,7-;/s3
InChIKey: FKVUDBWXNAFSPB-AUBOPKACNA-N
SMILES: C([C@H]1NC[C@@H]2C(C)(C)[C@H]12)(=O)OC.Cl |&1:1,4,8,r|

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Safety

HS Code: 2933998090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: M342865
Product name: (1R,2S,5S)-Methyl6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride
Packaging: 50mg
Price: $75
Updated: 2021/12/16

TRC

Product number: M342865
Product name: (1R,2S,5S)-Methyl6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride
Packaging: 10mg
Price: $60
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD22289
Product name: (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester hydrochloride
Packaging: 500mg
Price: $70
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CCH0007548
Product name: (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
Purity: 95.00%
Packaging: 0.5MG
Price: $825
Updated: 2021/12/16

Synthonix

Product number: M14329
Product name: Methyl(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride
Purity: 95+%
Packaging: 10g
Price: $910
Updated: 2021/12/16

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Boceprevir InterMediates Chemical Properties,Usage,Production

Uses

(1R, 2S, 5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate methyl ester hydrochloride is the cost in the side chain synthesis of boceprevir the highest key intermediate.

Uses

(1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride is an azabicyclohexane derivative used in the preparation of hepatitis C virus (HCV) NS3 serine protease inhibitor.

General Description

Boceprevir is a peptidomimetic protease inhibitor with four moieties, P1–P3 and a Cap, where P1 is a racemic β-aminoamide, P2 is a chiral dimethylcyclopropylproline analog, P3 is (S)-tert-leucine, and Cap is a tert-butylcarbamoyl group. The 3-azabicyclo[3.1.0]hexane structure of P2 adopts a constrained conformation, so that the gem-dimethyl group has a fixed angle with respect to the bicyclic ring structure. The incorporation of the 3-azabicyclo[3.1.0]hexane moiety results in a 1000-fold increase in NS3 protease binding over proline in a pentapeptide scaffold. When boceprevir binds to the NS3 protease, the P2 moiety interacts with four amino acid residues at the active site. The starting material for the P2 moiety is the HCl salt of the dimethylcyclopropylproline methyl ester 2. For medicinal chemistry studies, it was prepared by cyclopropanation of a Δ3-pyrroline derivative of pyroglutamic acid.

Synthesis

The amine oxidation was carried out in a RC-1 Process Development Workstation (Mettler Toledo) equipped with pH feedback control and a gas induction impeller. A solution of 2.5 g MAON401(Codexis), 7.0 g catalase (Novozyme), and 0.1 g Antifoam 204 in 255 mL phosphate buffer (pH 7.0, 20 mM) was charged to the reactor. The temperature was set at 25°C, and 3 N NaOH was added to adjust the pH to 7.4. Pure oxygen (4 psig, or 207 mmHg) was applied to the enzyme solution prior to substrate addition. The substrate solution was prepared by dissolving 50 g NaHSO3 (0.45 mol) and 40 g 6 (0.36 mol) in 240 mL water. The substrate solution was charged to the enzyme solution over 19 h while maintaining the pH at 7.4 by titration of 3 N NaOH. By the end of the addition, 56.5 g of 3 N NaOH (0.15 mol) had been added to the reaction mixture, and conversion was 96.4%. For cyanation, CPME (240 mL) was added to the stream (compound 5 and 7) from enzymatic step. The solution was chilled to 10°C. A solution of NaCN in 70 mL water (22.9 g, 0.45 mol) was added over 0.5 h. The cyanation reached > 98% conversion after additional 0.5 h at 10°C. Significant protein precipitation took place when cyanide was added. The insoluble was removed by filtration through celite. After phase split, the aqueous phase was back extracted with 100 mL CPME. In methanolysis step, the CPME solution of 8 was added to HCl in MeOH (260 mL, [HCl] ≥ 6 N) at 5-10°C over 1 h. The solution was heated to 50°C and agitated for 4 h to complete the conversion. For product isolation, the volume was reduced to 160 mL by evaporation, followed by extraction under basic condition to give a solution of 9 in MTBE (375 mL). In the final step, the product was isolated by crystallization after forming the HCl salt. The MTBE solution was added to HCl in a mixture of 60 mL iPrOH and 240 mL MTBE at 0°C. The solution was seeded to crystallize for 5 h at -10°C. After solid isolation and drying under vacuum, 41.2 g (0.20 mol, 56% overall yield) of 2 was obtained in >98.5% purity and >99.9% e.e.

Boceprevir InterMediates Preparation Products And Raw materials

Raw materials

Preparation Products

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Boceprevir InterMediates Suppliers

Canada 1 China 312 India 8 United Kingdom 1 United States 11 Global 333

EXON BIOPHARMA CO., LTD.

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View Lastest Price from Boceprevir InterMediates manufacturers

PNP Biotech Co. Ltd

Product: (1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride 565456-77-1
Price: US $0.00/kg
Min. Order: 25kg
Purity: 98%
Supply Ability: Inquiry
Release date: 2022-10-20

Hebei Duling International Trade Co. LTD

Product: (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE 565456-77-1
Price: US $60.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100 tons
Release date: 2022-10-10

Hebei Yanxi Chemical Co., Ltd.

Product: Boceprevir InterMediates 565456-77-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 20tons
Release date: 2023-10-08

565456-77-1, Boceprevir InterMediatesRelated Search:

Pregabalin Velpatasvir intermediate (1S,5R,6S)-Ethyl 5-(pentan-3-yl-oxy)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylate Entecavir hydrate Abacavir intermediate S)-3-Cyano-5-methyl hexanoic acid ethyl ester Boceprevir

(1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride

Boceprevir InterMediates

Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, (Hydrochloride), (1R,2S,5S)- (9CI)

(1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, hydrochloride, (1R,2S,5S)-

Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-diMethyl-,Methylester,hydrochloride(1:1),(1R,2S,5S)-

(1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester HCl

1.3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, methyl ester, hydrochloride(1R,2S,5S)

Boceprevir INT 1

(1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

5S)-6

6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

PF-07321332 intermediate

(1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORID

tert-butyl ((S)-1-cyano-2-((S)-2-oxopyrrolidin-3-yl)ethyl)carbamate

Paxlovid Int.

PF-07321332-002

(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

(1R,2S,5S)-Methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate HCl

(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochlorid

(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-...

(1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate acid Methyl ester hydrochloridee

Paxlovid Impurity 2

Nirmatrelvir intermediate 565456-77-1

Nirmatrelvir Intermediate

(1R.28,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2- CARBOXYLICACID METHYL ESTER HYDRoCHLORIDE

Paxlovid Intermediate 2

(1R,2S,5S)-6,6-dimethyl-3-aza-bicylo[3.1]hexane-2-carboxylic acid methyl ester hydrochloride

3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, methyl ester, hydrochloride (1:1), (1R,2S,5S)- (ACI)

Paxlovid Interediate

Intermediate of Boprevir

PF-07321332 Impurity 1

6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester hydrochloride

Nirmatrelvir Impurity 10 HCl

Methyl (1S,2S,5R)-1,5,6,6-tetramethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

Nirmatrelvir Impurity 29 HCl

565456-77-1

Boceprevir intermediate

Chiral Reagents

Heterocycles

Intermediates & Fine Chemicals

Pharmaceuticals

565456-77-1