Sodium Hydroxide → HCID 59977306, compound

HRID 393086Notes

Reaction equation

HRID 393086 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:29]=[C:28]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40]C(=O)C3C=C(F)C=C(F)C=3)[CH:35]=2)=[O:31])[CH:27]=[C:26]([CH3:51])[C:5]=1[C:6]([NH:8][C@H:9]([C:22]([O:24]C)=[O:23])[CH2:10][NH:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1)=[O:7]>CO>[Cl:3][C:4]1[CH:29]=[C:28]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([OH:40])[CH:35]=2)=[O:31])[CH:27]=[C:26]([CH3:51])[C:5]=1[C:6]([NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10][NH:11][C:12](=[O:21])[C:13]1[CH:14]=[C:15]([F:20])[CH:16]=[C:17]([F:19])[CH:18]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131723040HCID 131723040, compound

Product 1

HCID 59977306HCID 59977306, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (1 M; 0.123 mL, 0.123 mmol) was added to a solution of N-[2-chloro-4-[[[[3-[(3,5-difluorobenzoyl)oxy]phenyl]methyl]amino]carbonyl]-6-methylbenzoyl]-3-[(3,5-difluorobenzoyl)amino]-L-alanine, methyl ester (43 mg, 0.0614 mmol) in methanol (1 mL). The solution was allowed to stir overnight and then concentrated. The residue was purified by HPLC and lyophilized to give N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[(3,5-difluorobenzoyl)amino]-L-alanine (14.6 mg, 43%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-c1dedf318e44474184b134d477f49c21
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

Loading…