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

HRID 751700ノート

反応式

HRID 751700 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-66ff0aa997794a488124f1db00fe3925
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

反応ノート

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