CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)

Base Information

• Chemical Name: CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)
• CAS No.: 247068-81-1
• Molecular Formula: C14 H25 N O3
• Molecular Weight: 255.357
• Mol file: 247068-81-1.mol

Synonyms:(S)-tert-butyl 2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate; (S)-tert-butyl-2,6-dimethyl-3-oxohept-1-en-4-ylcarbamate; Carfilzomib intermediate; CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester; (S)-tert-butyl (2,6-dimethyl-3-oxohept-1-en-4-yl)carbamate;

Chemical Property of CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)

Chemical Property:

• Boiling Point: 350.4±25.0 °C(Predicted)
• PKA: 11.05±0.46(Predicted)
• PSA: 55.40000
• Density: 0.964±0.06 g/cm3(Predicted)
• LogP: 3.46190
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl((S)-2,6-Dimethyl-3-oxohept-1-en-4-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl ((S)-2,6-Dimethyl-3-oxohept-1-en-4-yl)carbamate is an intermediate in the synthesis of (S)-2-Amino-4-methyl-1-((S)-2-methyloxiran-2-yl)pentan-1-one Trifluoroacetate Salt which is an impurity of carfilzomib (C183460). Carfilzomib is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Technology Process of CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)

There total 14 articles about CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1-isobutyl-2-oxobutyl)carbamic acid tert-butyl ester → tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate (247068-81-1)

Guidance literature:

With piperidine; piperdinium acetate; In tetrahydrofuran; at 68 ℃; for 8h; Green chemistry;

DOI:10.3184/174751916X14539789662063

Reference yield: 92.0%

isopropenyllithium (6386-71-6) + N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide (87694-50-6) → tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate (247068-81-1)

Guidance literature:

In diethyl ether; at -78 ℃; for 2.5h;

Reference yield: 92.0%

isopropyllithium (1888-75-1) + N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide (87694-50-6) → tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate (247068-81-1)

Guidance literature:

In diethyl ether; at -78 ℃; for 2.5h;

DOI:10.1016/S0960-894X(99)00376-5

upstream raw materials:

isopropyllithium

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

isopropenyllithium

N-tert-butoxycarbonyl-L-leucine

Downstream raw materials:

C₁₆H₂₀BrNO₃

Carmaphycin A

Carmaphycin B

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate