N-(Cyclohexylcarbonyl)-D-phenylalanine

Base Information

• Chemical Name: N-(Cyclohexylcarbonyl)-D-phenylalanine
• CAS No.: 85856-40-2
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• DSSTox Substance ID: DTXSID501284731
• ChEMBL ID: CHEMBL33008
• Mol file: 85856-40-2.mol

Synonyms:CHEMBL33008;SCHEMBL4889588;DTXSID501284731;AKOS025635783;N-(Cyclohexylcarbonyl)-D-phenylalanine;N-(cyclohexyl-carbonyl)-d-phenylalanine;85856-40-2

Chemical Property of N-(Cyclohexylcarbonyl)-D-phenylalanine

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 275.15214353
• Heavy Atom Count: 20
• Complexity: 331

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(CC1)C(=O)NC(CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O

Technology Process of N-(Cyclohexylcarbonyl)-D-phenylalanine

There total 4 articles about N-(Cyclohexylcarbonyl)-D-phenylalanine 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: 97.0%

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) + cyclohexanylcarbonyl chloride (2719-27-9) → (R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid (85856-40-2)

Guidance literature:

With potassium phosphate; In tetrahydrofuran; for 24h; Inert atmosphere;

DOI:10.1021/ml200108y

Reference yield:

N-(Cyclohexylcarbonyl)-D-phenylalanine methyl ester → (R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid (85856-40-2)

Guidance literature:

With sodium hydroxide; In methanol; Yield given;

DOI:10.1021/jm00127a006

Reference yield:

D-phenylalanine methyl ester (21685-51-8) → (R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid (85856-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl₃, 3 h, 2) CHCl₃, 25 deg C, 1 d

2: 2N NaOH / methanol

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In methanol;

DOI:10.1021/jm00127a006

upstream raw materials:

D-(R)-phenylalanine

cyclohexanylcarbonyl chloride

D-phenylalanine methyl ester

Cyclohexanecarboxylic acid

Downstream raw materials:

(4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-phenylpropanoate

Refernces

• 1、 Shinkai,Nishikawa,Sato,Toi,Kumashiro,Seto,Fukama,Dan,Toyoshoma. "N-(Cyclohexylcarbonyl)-D-phenylalanines and related compounds. A new class of oral hypoglycemic agents. 2". . p. 1436 - 1441. Retrieved 2007/10/02.