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

HRID 1693446Notes

Reaction equation

HRID 1693446 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 (3×30 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 (3×30 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6216443b3faa411b85c22c1f5b3f2d22
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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