H-Tyr(Bzl)-OMe → 3-(4-Hydroxyphenyl)-2-(2-(4-biphenylcarbonyl)-phenylamino)-propionic acid methyl ester

HRID 1597462Notes

Reaction equation

HRID 1597462 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[NH2:5].[C:22]1([C:28]2[CH:42]=[CH:41][C:31]([C:32]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][C:35]3=O)=[O:33])=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH:5][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[C:32]([C:31]1[CH:30]=[CH:29][C:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:42][CH:41]=1)=[O:33])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 6999558H-Tyr(Bzl)-OMeHCID 217004172-(4-Phenylbenzoyl)cyclohexanone

Product 1

HCID 543635233-(4-Hydroxyphenyl)-2-(2-(4-biphenylcarbonyl)-phenylamino)-propionic acid methyl esterYield 32.3%

Procedure

The title compound (830 mg) was prepared from 1.83 g (5.7 mmol) O-benzyl-L-tyrosine methyl ester and 1.59 g (5.7 mmol) of 2-(4-phenylbenzoyl)cyclohexanone (Child, R. G. et.al. J. Pharm Sci 1977, 66(4), 466-76) according to the method of Intermediate 23 followed by purification via silica gel chromatography eluting with 1/9 EtOAc/hexanes: Low resolution MS (Cl) m/e 452 (MH+).

Workup

  1. customfollowed by purification via silica gel chromatography
  2. washeluting with 1/9 EtOAc/hexanes

Sources & evidence

ORD record
ord-dfb1ea8e85ef42f69229b791421f043a
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

Loading…