Sodium Hydroxide → (S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737190Notes

Reaction equation

HRID 737190 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[O:24][C:25]([C:28]([O:30]C)=[O:29])=[CH:26][CH:27]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[O:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86616436(S)-2-[4-(5-Methoxycarbonyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 86616437(S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Procedure

Hydrolysis of (S)-2-[4-(5-Methoxycarbonyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (0.350 g, 0.77 mmol) with NaOH (1M, 2 mL, 2 mmol) gave (S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester; MS: 442.1 (M+H+).

Sources & evidence

ORD record
ord-dd04cd8e4ef2478e8acf03dd2b8019c8
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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