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

HRID 751700Notes

Reaction equation

HRID 751700 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])[C@H:6]([OH:28])[C@@H:7]([NH:15][C:16]([C:18]1[NH:27][C:21]2=[CH:22][N:23]=[C:24]([Cl:26])[CH:25]=[C:20]2[CH:19]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[Cl:26][C:24]1[CH:25]=[C:20]2[CH:19]=[C:18]([C:16]([NH:15][C@@H:7]([CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C@@H:6]([OH:28])[C:5]([OH:29])=[O:4])=[O:17])[NH:27][C:21]2=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59753593(S)-3-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acid methyl ester

Product 1

HCID 59753553(S)-3-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (0.24 mL, 2M, 0.48 mmol) was added to a solution of (S)-3-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acid methyl ester (EXAMPLE 43, 170 mg, 0.44 mmol) in methanol (5 mL) and the reaction stirred at rt for 24 h. The solvent was removed in vacuo and the residue partitioned between hydrochloric acid (1N, 30 mL) and ethyl acetate (3×3 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid. δH (DMSO): 2.71 (1H, dd), 2.91 (1H, dd), 3.56 (1H, d), 4.38–4.46 (1H, m), 4.77 (1H, s), 6.76 (1H, s), 7.11–7.16 (1H, m), 7.19–7.27 (4H, m), 7.45 (1H, s), 8.44–8.52 (2H, m); m/z (ES+)=374 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between hydrochloric acid (1N, 30 mL) and ethyl acetate (3×3 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66ff0aa997794a488124f1db00fe3925
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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