2-(4-Methoxybenzoyl)cyclohexanone → 3-(4-Hydroxyphenyl)-2-(2-(4-methoxybenzoyl)-phenylamino)-propionic acid methyl ester

HRID 1597463Notes

Reaction equation

HRID 1597463 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:19][O:20][C:21](=[O:39])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31]CC2C=CC=CC=2)=[CH:27][CH:26]=1)[NH2:23]>>[CH3:19][O:20][C:21](=[O:39])[CH:22]([NH:23][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7](=[O:8])[C:6]1[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 2444182-(4-Methoxybenzoyl)cyclohexanoneHCID 12616037H-Tyr(Bzl)-OMe.HCl

Product 1

HCID 545390133-(4-Hydroxyphenyl)-2-(2-(4-methoxybenzoyl)-phenylamino)-propionic acid methyl esterYield 28.5%

Procedure

The title compound (2.31 g) was prepared from 4.64 g (20 mmol) of 2-(4-methoxybenzoyl)-cyclohexanone (Howard, A. S. et. al. Tetrahedron Lett. 1979, (15), 1339-40) and 6.43 g (20 mmol) of O-benzyl-L-tyrosine methyl ester hydrochloride as a yellow solid as described for Intermediate 161: low resolution MS (Cl) m/e 406 (MH+).

Sources & evidence

ORD record
ord-b9a3cdfe379a4afebbbdcd554be799e2
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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