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
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
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.
N-Bromosuccinimide Price
- 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
- 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
- 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
- Product number
- AAA0035296
- Product name
- TERT-BUTYL N-[(2S)-4-METHYL-1-[(2R)-2-METHYLOXIRAN-2-YL]-1-OXOPENTAN-2-YL]CARBAMATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $457.06
- Updated
- 2021/12/16
- 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
- 5g
- Price
- $514
- Updated
- 2021/12/16
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
CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester Suppliers
- Tel
- +49-7246-3082843
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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
- 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
- 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