Tert-butyl 3-amino-3-cyano-2-methylpropanoate

Base Information

• Chemical Name: Tert-butyl 3-amino-3-cyano-2-methylpropanoate
• CAS No.: 194156-55-3
• Molecular Formula: C₉H₁₆N₂O₂
• Molecular Weight: 184.238
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID40692948
• Mol file: 194156-55-3.mol

Synonyms:DTXSID40692948;BOC-L-ASPARTIMOLT-BUTYLESTER;tert-butyl 3-amino-3-cyano-2-methylpropanoate;tert-butyl 3-amino-3-cyano-2-methyl-propanoate;A813706;3-amino-3-cyano-2-methylpropanoic acid tert-butyl ester

Chemical Property of Tert-butyl 3-amino-3-cyano-2-methylpropanoate

Chemical Property:

• PSA: 62.12000
• LogP: 2.20418
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 184.121177757
• Heavy Atom Count: 13
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

3-Boc-aminobutyronitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C#N)N)C(=O)OC(C)(C)C

Technology Process of Tert-butyl 3-amino-3-cyano-2-methylpropanoate

There total 24 articles about Tert-butyl 3-amino-3-cyano-2-methylpropanoate 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: 91.5%

→ (2-cyano-1(R)-methylethyl)carbamic acid, 1,1-dimethylethyl ester (170367-68-7,194156-55-3) + (3-amino-1(R)-methylpropyl)carbamic acid, 1,1-dimethylethyl ester (170367-69-8,177489-90-6)

Guidance literature:

Reference yield: 86.0%

sodium cyanide (773837-37-9) + (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate (126301-16-4) → (2-cyano-1(S)-methylethyl)carbamic acid, 1,1-dimethylethyl ester (172695-22-6,194156-55-3)

Guidance literature:

In N,N-dimethyl-formamide; at 90 ℃; for 1h;

DOI:10.1039/c5ob01692d

Reference yield: 84.0%

(2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate (126301-16-4) → (2-cyano-1(S)-methylethyl)carbamic acid, 1,1-dimethylethyl ester (172695-22-6,194156-55-3)

Guidance literature:

sodium cyanide; With tetrabutylammomium bromide; In DMF (N,N-dimethyl-formamide); at 35 ℃; for 2.5h;

(2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate; In DMF (N,N-dimethyl-formamide); at 35 ℃;

upstream raw materials:

tetraethylammoniumcyanide

tert-butyl N-[(1S)-2-iodo-1-methylethyl]carbamate

sodium cyanide

(S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane

Downstream raw materials:

(S)-methyl 3-aminobutanoate

(S)-methyl 3-(tert-butyloxycarbonylamino)butyrate

(2-cyano-1(S)-methylethyl)carbamic acid, 1,1-dimethylethyl ester

(2-cyano-1(R)-methylethyl)carbamic acid, 1,1-dimethylethyl ester