Sodium Hydroxide → 4-[4-(3-Indolyl)piperidinomethyl]-2-glycoloylaminothiazole

HRID 1252079Notes

Reaction equation

HRID 1252079 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:29])[CH2:24][O:25]C(=O)C)[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.[OH-].[Na+]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:29])[CH2:24][OH:25])[S:20][CH:21]=3)[CH2:14][CH2:15]2)=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 141297994-[4-(3-Indolyl)piperidinomethyl]-2-(2-acetoxyacetylamino)thiazole

Product 1

HCID 141298054-[4-(3-Indolyl)piperidinomethyl]-2-glycoloylaminothiazoleYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-[4-(3-indolyl)piperidinomethyl]-2-(2-acetoxyacetylamino)thiazole (0.9 g) in ethanol (20 ml) was added 1N aqueous solution of sodium hydroxide (3 ml). After one hour of stirring, the reaction mixture was concentrated and the resulting precipitate was collected by filtration and recrystallized from a mixture of water and ethanol to give 4-[4-(3-indolyl)piperidinomethyl]-2-glycoloylaminothiazole (0.28 g).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. filtrationthe resulting precipitate was collected by filtration
  3. customrecrystallized from a mixture of water and ethanol

Sources & evidence

ORD record
ord-f8b177ca19dd43c4bacff1b125b8ecc9
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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