Methyl Benzoate → 3-{4-[3-Biphenyl-2-ylmethyl-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2(R)-hydroxypropionic acid

HRID 967658

Reaction equation

HRID 967658 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[C:12](=[O:15])[NH:13]Cl)=[CH:6][CH:5]=1.[C:29]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35]N.COC(=O)C1C=CC=CC=1.Cl.C([O:56][C:57](=[O:62])[C@H:58]([OH:61])[CH2:59][NH2:60])C>>[C:29]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][NH:13][C:12](=[O:15])[N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([NH:60][CH2:59][C@@H:58]([OH:61])[C:57]([OH:62])=[O:56])=[O:28])=[CH:9][CH:8]=1)[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 7150Methyl BenzoateHCID 2633661-Biphenyl-2-ylmethanamineHCID 86586062N-chlorocarbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl esterHCID 86586063(R)-isoserine ethyl ester hydrochloride

Product 1

HCID 102581063-{4-[3-Biphenyl-2-ylmethyl-1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}-2(R)-hydroxypropionic acid

Procedure

This compound was prepared similarly as described in example 35 from N-chlorocarbamoyl-4-[(4-cyclohexylphenylamino)methyl]benzoic acid methyl ester and biphenyl-2-ylmethylamine followed by hydrolysis of the benzoic acid methyl ester, coupling with (R)-isoserine ethyl ester hydrochloride. Hydrolysis afforded the title compound.

Workup

  1. customThis compound was prepared similarly
  2. customHydrolysis

Sources & evidence

ORD record
ord-2ea6fb38742a4e0eb38897400ba16f29
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Linked notes

Loading…