ChemicalBook > CAS DataBase List > BOC-PYR-OET

BOC-PYR-OET

Product Name: BOC-PYR-OET
CAS No.: 144978-12-1
Chemical Name: BOC-PYR-OET
Synonyms: Saxaint-B;Boc-L-Pyr-OEt;Boc-Pyr-Oet-OH;utamic Acid EthyL;cas no.341031-54-7;BOC-PYR-OET USP/EP/BP;Velpatasvir Impurity 37;Ethyl-N-Boc-Pyroglutamate;S-Ethyl-N-Boc-pyroglutamase;Ethyl N-Boc-L-pyroglutamate
CBNumber: CB1511426
Molecular Formula: C12H19NO5
Formula Weight: 257.28
MOL File: 144978-12-1.mol

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BOC-PYR-OET Property

Melting point:: 52.0 to 56.0 °C
Boiling point:: 375.0±35.0 °C(Predicted)
Density: 1.182±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: soluble in Methanol
form: powder to crystal
pka: -4.15±0.40(Predicted)
color: White to Almost white
InChI: InChI=1S/C12H19NO5/c1-5-17-10(15)8-6-7-9(14)13(8)11(16)18-12(2,3)4/h8H,5-7H2,1-4H3/t8-/m0/s1
InChIKey: YWWWGFSJHCFVOW-QMMMGPOBSA-N
SMILES: N1(C(OC(C)(C)C)=O)C(=O)CC[C@H]1C(OCC)=O
CAS DataBase Reference: 144978-12-1(CAS DataBase Reference)

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Safety

HS Code: 2933.99.8290

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

TCI Chemical

Product number: E1135
Product name: Ethyl N-(tert-Butoxycarbonyl)-L-pyroglutamate
Purity: >97.0%(HPLC)(N)
Packaging: 1g
Price: $20
Updated: 2025/07/31

TCI Chemical

Product number: E1135
Product name: Ethyl N-(tert-Butoxycarbonyl)-L-pyroglutamate
Purity: >97.0%(HPLC)(N)
Packaging: 5g
Price: $50
Updated: 2025/07/31

TRC

Product number: B690945
Product name: N-tert-ButoxycarbonylpyroglutamicAcidEthylEster
Packaging: 50g
Price: $745
Updated: 2021/12/16

Matrix Scientific

Product number: 153098
Product name: (S)-1-tert-Butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate
Purity: 95%
Packaging: 100g
Price: $1046
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB39596
Product name: N-Boc-L-pyroglutamic acid etHyl ester
Packaging: 100g
Price: $120
Updated: 2021/12/16

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BOC-PYR-OET Chemical Properties,Usage,Production

Uses

N-tert-Butoxycarbonylpyroglutamic Acid Ethyl Ester is a compound derived from pyroglutamic acid, used in the synthesis of various pharmacological compounds. It is used in the synthesis of HCV protesase inhibitors as well as alkyl renin inhibitors.

General Description

BOC-PYR-OET [also known as 1-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate] is an organic ester compound that can be used as a pharmaceutical intermediate for the synthesis of drugs such as Avibactam, Velpatasvir and CETP inhibitors (MK-8262).

Synthesis

24424-99-5

7149-65-7

144978-35-8

Step 1. Synthesis of ethyl Boc-D-pyroglutamate: the title compound was prepared by literature method or by the following modified steps. Firstly, ethyl L-pyroglutamate was used as starting material for the N-protection reaction with di-tert-butyl dicarbonate (Boc2O) in dichloromethane in the presence of catalytic amount of DMAP to obtain N-Boc-L-pyroglutamic acid ethyl ester. Subsequently, ethyl N-Boc-L-pyroglutamate was dissolved in toluene and treated with lithium triethylborohydride (LiEt3BH) at -78 °C for the carbonyl reduction reaction. Upon completion of the reaction, 2,6-dimethylpyridine (lutidine) and a catalytic amount of DMAP were added, followed by the dehydration reaction by dropwise addition of trifluoroacetic anhydride (TFAA) to produce ethyl 4,5-dehydroproline. Finally, the target product Boc-D-pyroglutamic acid ethyl ester was obtained by cyclopropanation reaction (using Et2Zn and ClCH2I in 1,2-dichloroethane, -15 °C). The detailed steps are described below: Synthesis of ethyl 4,5-dehydro-L-proline: ethyl L-pyroglutamate (200 g, 1.27 mol) was dissolved in 1.2 L of dichloromethane, and di-tert-butyl dicarbonate (297 g, 1.36 mol) and a catalytic amount of DMAP (1.55 g, 0.013 mol) were added sequentially and reacted for 6 h at room temperature. After completion of the reaction, it was quenched with saturated brine and the organic phase was dried over anhydrous Na2SO4 and filtered through a short silica gel column to give 323 g (100%) of ethyl N-Boc-L-pyroglutamate. Ethyl N-Boc-L-pyroglutamate (160 g, 0.62 mol) was dissolved in 1 L of toluene, cooled to -78 °C, and lithium triethylborohydride (666 mL, 1.0 M THF solution) was added slowly dropwise over 90 min. After 3 hr of reaction, 2,6-dimethylpyridine (423 mL, 3.73 mol) and DMAP (0.2 g, 0.0016 mol) were added, followed by dropwise addition of TFAA (157 g, 0.74 mol), and the reaction mixture was brought to room temperature within 2 hr. The reaction mixture was diluted with EtOAc and water, and the organic phase was washed sequentially with 3N HCl, water, saturated NaHCO3 solution, and brine, dried over anhydrous Na2SO4, and filtered through a silica plug to give 165 g of crude product. The crude product was purified by fast column chromatography on silica gel with eluent of 1:5 ethyl acetate:hexane to give 120 g (75%) of ethyl 4,5-dehydroproline.

References

[1] Patent: US2008/9497, 2008, A1. Location in patent: Page/Page column 70-71
[2] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0138; 0139
[3] Organic Preparations and Procedures International, 2001, vol. 33, # 4, p. 405 - 409
[4] Organic and Biomolecular Chemistry, 2006, vol. 4, # 21, p. 3894 - 3897
[5] Patent: US2011/34438, 2011, A1. Location in patent: Page/Page column 25-26

BOC-PYR-OET Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from BOC-PYR-OET manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD

Product: Boc-L-Pyroglutamic acid ethyl ester 144978-12-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000kg
Release date: 2025-05-07

WUHAN FORTUNA CHEMICAL CO., LTD

Product: BOC-PYR-OET 144978-12-1
Price: US $0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 10 tons
Release date: 2021-08-09

Sichuan HongRi Pharma-Tech Co.,Ltd

Product: Boc-L-Pyroglutamic acid ethyl ester/ Boc-Pyr-Oet 144978-12-1
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1T+
Release date: 2023-10-11

144978-12-1, BOC-PYR-OETRelated Search:

L-Pyroglutamic acid Avibactam impurity 23 Boc-L-homophenylalanine BOC-L-Leucine BOC-L-Phenylglycinol Boc-Lys(Boc)-OH N-alpha-t-Butyloxycarbonyl-N-epsilon-benzyloxycarbonyl-L-lysinol N-Boc-N'-Cbz-L-lysine N-Boc-L-Phenylalaninol BOC-L-LEUCINOL Avibactam Impurity 21 Avibactam impurity 24 Avibactam Impurity 13 Avibactam Impurity 19 O-Benzylhydroxylamine Trans-5-(Benzyloxyamino)piperidine-2-carboxylic acid Ethyl L-pyroglutamate BOC-PYR-OH

(2S)-5-oxo-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-ethyl ester

Boc-L-Pyroglutamic acid ethyl ester/ Boc-Pyr-Oet

1-(tert-butyl)2-ethyl(S)-5-oxopyrrolidine-1,2-dicarboxylate

Ethyl (S)-1-Boc-5-oxopyrrolidine-2-carboxy

N-Boc-L-pyroglutamic acid ethyl este

(S)-N-alpha-t-Butyloxycarbonyl-pyroglutamic acid ethyl ester

Boc-L-Pyr-OEt

N-tert-Butoxycarbonyl-L-pyroglutamic acid ethyl ester

1-BOC-L-PYROGLUTAMIC ACID ETHYL ESTER

N-Boc-L-pyroglutamic acid ethyl ester

(S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Ethyl-N-Boc-Pyroglutamate

(S)-1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate

S-Ethyl-N-Boc-pyroglutamase

N-tert-ButoxycarbonylpyroglutaMic acid ethyl ester

Ethyl (S)-N-(tert-butoxycarbonyl)pyroglutaMate

Ethyl (S)-1-Boc-5-oxopyrrolidine-2-carboxylate

1-Boc-L-PyroglutaMicacidethylester/(S)-1-tert-butyl2-ethyl5-oxopyrrolidine-1,2-dicarboxylate

1,2-Pyrrolidinedicarboxylicacid, 5-oxo-, 1-(1,1-diMethylethyl

Ethyl N-(tert-Butoxycarbonyl)-L-pyroglutamate

1-tert-butyl 2-ethyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate

Saxaint-B

N-Boc-L-Pyroglutamic Acid Ethyl Ester (Boc-Pyr-Oet)

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

cas no.341031-54-7

Boc-L-Pyroglutamic acid ethyl este

Avibactam related impurities 1

Ethyl N-(tert-Butoxycarbonyl)-L-pyroglutamate &gt

Avibartan Related Impurity 1

utamic Acid EthyL

1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, 1-(1,1-dimethylethyl) 2-ethyl ester, (2S)-

(S)-1-(tert-Butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic Acid Ethyl Ester

Ethyl (S)-1-(tert-Butoxycarbonyl)-5-oxopyrrolidine-2-carboxylate

Ethyl N-Boc-L-pyroglutamate

N-Boc-L-pyroglutamic Acid Ethyl

BOC-PYR-OET USP/EP/BP

Ethyl t-butoxycarbonyl-l-pyroglutamate

Boc-l-pyroglutamate ethyl ester

1-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Velpatasvir Impurity 37

Boc-Pyr-Oet-OH

Boc-L-pyroglutamicacidester

N-Boc-pyroglutamic acid ethyl ester

1-(tert-Butyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

144978-12-1

C12H19NO5

pharmacetical

Pyroglutamic acid [Pyr, pGu]