Potassium Hydroxide → HCID 69693721, compound

HRID 583787Notes

Reaction equation

HRID 583787 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]([C:12]2[S:13][C:14]([C:23]([O:25]CC)=[O:24])=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)=[O:11])[CH2:4]1.C1COCC1.C(O)C.[Na].[OH-].[K+]>C(O)C>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]([C:12]2[S:13][C:14]([C:23]([OH:25])=[O:24])=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)=[O:11])[CH2:4]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 5360545SodiumHCID 21873804Tetrahydrofuran ethanolHCID 86759789HCID 86759789, compound

Product 1

HCID 69693721HCID 69693721, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a stirred solution of (±)-2-(3-methoxycyclopentylmethylcarboxy)-4-phenyl-thiazol-5-carboxylic acid, ethyl ester (0.01 mol), which may be prepared as described in Step (d) above, in a solvent such as ethanol, aqueous ethanol, or THF-ethanol, is added a solution of sodium or potassium hydroxide in ethanol at a concentration of from 1 M to about 2 M, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the mixture is rotary evaporated to remove most of the organic solvents, and the concentrated mixture is washed with ethyl acetate. The aqueous layer is acidified with hydrochloric acid to a pH of about 2 to about 4, and the product which precipitates is filtered off to give (±)-2-(3-methoxycyclopentylmethylcarboxy)-4-phenyl-thiazol-5-carboxylic acid, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. customReaction progress

Sources & evidence

ORD record
ord-fa8f84f56d6a40c9ae0e751df22791c3
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

Loading…