(2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride

Base Information

• Chemical Name: (2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride
• CAS No.: 631914-55-1
• Molecular Formula: C8H14ClNO3
• Molecular Weight: 207.657
• DSSTox Substance ID: DTXSID70460490
• Wikidata: Q82284546
• Mol file: 631914-55-1.mol

Synonyms:631914-55-1;(2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride;SCHEMBL3886760;DTXSID70460490;SDBQPOCLUYDXKE-YFKPBYRVSA-N

Chemical Property of (2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride

Chemical Property:

• Boiling Point: 271.3±23.0 °C(Predicted)
• PKA: 10.98±0.46(Predicted)
• PSA: 58.89000
• Density: 1.142±0.06 g/cm3(Predicted)
• LogP: 1.86940
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.0662210
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride

There total 3 articles about (2S)-2-[(tert-butoxycarbonyl)amino]propionyl chloride 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:

L-N-Boc-Ala (15761-38-3) + 1,1-dichloro-2,3-dimesitylcyclopropene (950916-77-5) → bis(2,4,6-trimethylphenyl)cyclopropenone (61440-88-8) + Boc-L-Ala-Cl (631914-55-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 23 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1021/ja101292a

Reference yield:

L-N-Boc-Ala (15761-38-3) → Boc-L-Ala-Cl (631914-55-1)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1021/jm00402a034

Reference yield:

6-chloro-4-hydrazinopyrimidine (5767-35-1) + ethyl (Z)-N-[(2S)-2-(tert-butoxycarbonylamino)propanoyl]cyclopropanecarboximidate → Boc-L-Ala-Cl (631914-55-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 16h;

upstream raw materials:

L-N-Boc-Ala

1,1-dichloro-2,3-dimesitylcyclopropene

6-chloro-4-hydrazinopyrimidine

Downstream raw materials:

N-tert-butyloxycarbonylalanylphenylalanine methyl ester

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

(S)-3-[(tert-butoxy)carbonylamino]-1-diazobutan-2-one

tert-butyl ((S)-1-(((1S,2S)-2-hydroxy-1,2-diphenylethyl)(methyl)amino)-1-oxopropan-2-yl)carbamate

Refernces

• 1、 Boudreault, Pierre-Luc,Comeau, Christian,Derbali, Rabeb Mouna,Grandbois, Michel,Poulet, Sylvain,Ries, Benjamin,Riniker, Sereina,Sarret, Philippe,Stadelmann, Thomas,Tremblay, Jacob,C?té, Jér?me,Fr?hlich, Ulrike,Leclair, Grégoire,Marsault, éric. "Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- And C-Methylations Fine-Tune Conformation and Properties". . p. 5365 - 5383. Retrieved 2021/05/04.
• 2、 Vathsala,Srinivasulu,Santhosh,Sureshbabu, Vommina V.. "The synthesis of Nα-protected amino hydroxamic acids from Nα-protected amino acids employing versatile chlorinating agent CPI-Cl". . p. 449 - 457. Retrieved 2019/03/08.