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

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:

(alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI) benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate

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