Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester
• CAS No.: 172695-23-7
• Molecular Formula: C₁₁H₂₀N₂O₂
• Molecular Weight: 212.292
• DSSTox Substance ID: DTXSID301165406
• Mol file: 172695-23-7.mol

Synonyms:172695-23-7;Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester;TERT-BUTYL N-[(2R)-1-CYANO-3-METHYLBUTAN-2-YL]CARBAMATE;SCHEMBL18055375;DTXSID301165406;EN300-7038074;1,1-Dimethylethyl N-[(1R)-1-(cyanomethyl)-2-methylpropyl]carbamate

Chemical Property of Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester

Chemical Property:

• PSA: 62.12000
• LogP: 2.84028
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 212.152477885
• Heavy Atom Count: 15
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC#N)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](CC#N)NC(=O)OC(C)(C)C

Technology Process of Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester

There total 12 articles about Carbamic acid, [(1R)-1-(cyanomethyl)-2-methylpropyl]-, 1,1-dimethylethyl ester 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: 82.0%

tetraethylammoniumcyanide (13435-20-6) + (S)-(1-iodomethyl-2-methylpropyl)carbamic acid tert-butyl ester (161529-21-1) → (R)-3-<(tert-butoxycarbonyl)amino>-4-methylpentanenitrile (172695-23-7)

Guidance literature:

In dichloromethane; for 4h; Heating;

DOI:10.1016/0040-4020(95)00778-7

Reference yield: 72.0%

sodium cyanide (143-33-9,25596-52-5) + (S)-2-(N-tert-butoxycarbonylamino)-3-methylbutyl tosylate (122818-28-4) → (R)-3-<(tert-butoxycarbonyl)amino>-4-methylpentanenitrile (172695-23-7)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/chem.200500121

Reference yield: 43.0%

sodium cyanide (773837-37-9) + [(2S)-2-(tert-butoxycarbonylamino)-3-methyl-butyl] methanesulfonate (126301-18-6,109687-64-1) → (R)-3-<(tert-butoxycarbonyl)amino>-4-methylpentanenitrile (172695-23-7)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 1h;

DOI:10.1016/j.tetasy.2009.07.045

upstream raw materials:

tetraethylammoniumcyanide

(S)-(1-iodomethyl-2-methylpropyl)carbamic acid tert-butyl ester

sodium cyanide

[(2S)-2-(tert-butoxycarbonylamino)-3-methyl-butyl] methanesulfonate

Downstream raw materials:

(R)-3-amino-4-methylpentanoic acid

(2S)-2-isopropyl-4,6-dioxopiperidine

Refernces

• 1、 -. "DESACETOXYTUBULYSIN H AND ANALOGS THEREOF". . . Retrieved 2016/09/22.
• 2、 Sohtome, Yoshihiro,Shin, Bongki,Horitsugi, Natsuko,Takagi, Rika,Noguchi, Keiichi,Nagasawa, Kazuo. "Entropy-controlled catalytic asymmetric 1,4-type Friedel-crafts reaction of phenols using conformationally flexible guanidine/bisthiourea organocatalyst". supporting information; experimental part. p. 7299 - 7303. Retrieved 2010/11/04.