CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester

Product Name: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
CAS No.: 247068-82-2
Chemical Name: CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
Synonyms: Boc-L-leucine epoxyketone;EOS-60549;CFE-4B (Carfilzomib);PR171 intermedaite I;Boc-leucine-epoxyketone;CarfilzomibIntermediateB;ert-Butyl ((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopen;[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carb...;N-Boc-2(S)-Amino-4-methyl-1-[(2R)-methyl-oxiranyl]-pentan-1-one;[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carbamic
CBNumber: CB32665457
Molecular Formula: C14H25NO4
Formula Weight: 271.35
MOL File: 247068-82-2.mol

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CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester Property

Boiling point:: 369.8±37.0 °C(Predicted)
Density: 1.061±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
pka: 11.08±0.46(Predicted)
Appearance: White to yellow <39°C Solid,>41°C Liquid
InChI: InChI=1S/C14H25NO4/c1-9(2)7-10(11(16)14(6)8-18-14)15-12(17)19-13(3,4)5/h9-10H,7-8H2,1-6H3,(H,15,17)/t10-,14+/m0/s1
InChIKey: DDMPMIMTLBGEHT-IINYFYTJSA-N
SMILES: C(OC(C)(C)C)(=O)N[C@H](C([C@@]1(C)CO1)=O)CC(C)C

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

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

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: B809210
Product name: tert-Butyl((S)-4-Methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
Packaging: 500mg
Price: $1045
Updated: 2021/12/16

AK Scientific

Product number: 6856DN
Product name: Tert-butyl((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
Packaging: 100mg
Price: $1701
Updated: 2021/12/16

AK Scientific

Product number: 6856DN
Product name: Tert-butyl((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
Packaging: 500mg
Price: $1807
Updated: 2021/12/16

ChemScene

Product number: CS-M2423
Product name: tert-Butyl((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
Purity: 99.78%
Packaging: 250mg
Price: $69
Updated: 2021/12/16

ChemScene

Product number: CS-M2423
Product name: tert-Butyl((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate
Purity: 99.78%
Packaging: 1g
Price: $171
Updated: 2021/12/16

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CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester Chemical Properties,Usage,Production

Uses

tert-Butyl ((S)-4-Methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate is an intermediate of Carfilzomib (C183460) which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Synthesis

247068-81-1

247068-82-2

The general procedure for the synthesis of tert-butyl N-[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxo-2-pentyl]carbamate from tert-butyl (S)-(2,6-dimethyl-3-oxohept-1-en-4-yl)carbamate is as follows: tert-butyl (S)-(2,6-dimethyl-3-oxohept-1-en-4-yl) tert-butyl carbamate (102 g, 0.4 mol) and asymmetric chiral catalyst (R)-La-BINOL (3.24 g, 2 mol%) were added to a 1 L reaction flask, followed by triphenylphosphine (14.8 g, 20 mol%) and 500 mL of toluene and stirred at room temperature. Subsequently, tert-butanol (108 g, 1.2 mol) was added slowly and dropwise. After 0.5 h of reaction, the progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered and the filtrate was collected. The filtrate was quenched with 300 mL of saturated sodium sulfite solution. Tetrahydrofuran was removed by evaporation under reduced pressure and then extracted with 400 mL of ethyl acetate. The organic phase was washed sequentially with 100 mL of water and 100 mL of saturated saline, dried over anhydrous sodium sulfite, and concentrated under reduced pressure to give 92 g of a pale yellow oil, the target product N-[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxo-2-pentyl]carbamic acid tert-butyl ester in a yield of 85.0% with an ee value of 93%.

References

[1] Patent: CN104672179, 2017, B. Location in patent: Paragraph 0009; 0024; 0025; 0027-0043
[2] Patent: WO2018/100050, 2018, A1. Location in patent: Page/Page column 15; 16; 17; 18
[3] ChemBioChem, 2012, vol. 13, # 6, p. 810 - 817
[4] Patent: WO2013/9923, 2013, A1. Location in patent: Sheet 4; 5
[5] Bioorganic and Medicinal Chemistry, 2018,

CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester Suppliers

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View Lastest Price from CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester manufacturers

Changzhou Rokechem Technology Co., Ltd.

Product: tert-Butyl ((s)-4-methyl-1-((r)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)carbamate 247068-82-2
Price: US $0.00-0.00/Kg
Min. Order: 1Kg
Purity: 97%
Supply Ability: 1-10000kgs
Release date: 2023-06-12

Career Henan Chemical Co

Product: Boc-L-leucine epoxyketone 247068-82-2
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1000KG
Release date: 2019-09-04

247068-82-2, CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl esterRelated Search:

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tert-butyl 4-methyl-1-(2-methyloxiran-2-yl)-1-oxopentan-2-ylcarbamate

tert-butyl N-[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamate

EOS-60549

ert-butylN-[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamate

((1S)-3-METHYL-1-(((2R)-2-METHYLOXRANYL)CARBONYL)BUTYL)CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

ert-Butyl ((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopen

CFE-4B (Carfilzomib)

[(1S)-3-Methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]carb...

PR171 intermedaite I

N-Boc-2(S)-Amino-4-methyl-1-[(2R)-methyl-oxiranyl]-pentan-1-one

CarbaMic acid,N-[ (1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxira-nyl]carbony1] -, 1,1-diMethyl ethy1 ester

CarfilzomibIntermediateB

(2S)-2-(Boc-amino)-4-Methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentane ee

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247068-82-2