Sodium Hydroxide → 3-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid

HRID 751712Notes

Reaction equation

HRID 751712 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([OH:26])[C@@H:5]([NH:13][C:14]([C:16]1[NH:25][C:19]2=[CH:20][N:21]=[C:22]([Cl:24])[CH:23]=[C:18]2[CH:17]=1)=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[Cl:24][C:22]1[CH:23]=[C:18]2[CH:17]=[C:16]([C:14]([NH:13][C@@H:5]([CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C@H:4]([OH:26])[C:3]([OH:27])=[O:2])=[O:15])[NH:25][C:19]2=[CH:20][N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 112462123-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid methyl ester

Product 1

HCID 111879523-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(S)-hydroxy-4-phenylbutyric acid methyl ester (152 mg, 0.39 mmol) was hydrolysed in a similar way to EXAMPLE 44 using sodium hydroxide solution (0.44 ml, 1N, 0.44 mmol) in methanol (10 mL). δH (d6 DMSO): 2.83, 2.95 (2H, 2dd), 4.19 (1H, d), 4.52 (1H, m), 5.75 (1H, br s), 7.10-7.33 (6H, 2m), 7.68 (1H, s), 8.54 (1H, s), 8.72 (1H, d).

Sources & evidence

ORD record
ord-47c487fd082a4e7db340eee9b41ed4a9
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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