Lithium Hydroxide → 2-(3-Hydroxy-2-pyridinyl)-4-thiazoleacetic Acid

HRID 260282Notes

Reaction equation

HRID 260282 reaction equation
OC1C=CC=CC=1C1SC=C(CC(O)=O)N=1.C([O:19][C:20](=[O:34])[CH2:21][C:22]1[N:23]=[C:24]([C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[S:25][CH:26]=1)C.[Li+].[OH-]>>[OH:33][C:32]1[C:27]([C:24]2[S:25][CH:26]=[C:22]([CH2:21][C:20]([OH:34])=[O:19])[N:23]=2)=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 1357374432-(2-Hydroxyphenyl)-4-thiazoleacetic AcidHCID 1359793022-(3-Hydroxy-2-pyridinyl)-4-thiazoleacetic Acid Ethyl Ester

Product 1

HCID 1357374422-(3-Hydroxy-2-pyridinyl)-4-thiazoleacetic AcidYield 99%

Procedure

The procedure used for the preparation of 5a was repeated with 4c (335 mg, 1.27 mmol) and 2N LiOH (2.22 mL) to provide 5c (296 mg, 99%) as a white solid, which was recrystallized from EtOAc/hexane. mp 175.0°-176.0° C.; IR KBr) 3450, 3300-2500 (br), 1729, 1697, 1449, 1189 cm-1 ; 1H NMR (DMSO-d6) δ 3.83 (2H s, CH2), 7.37 (1H dd, J=8.5 and 4.4 Hz, Ar), 7.44 (1H, d, J=8.5 Hz, Ar), 7.63 (1H, s), 8.14 (1H, d, J=4.4 Hz, Ar), 11.70 (1H, s, OH), 12.54 (1H, s, CO2H); FDMS m/z 237 (M+ +1); Anal. Calcd for C10H8N2O3S: C, 50.84; H, 3.41; N, 11.86. Found: C, 50.77; H, 3.42; N, 11.74.

Sources & evidence

ORD record
ord-e38a7a828bb84451b0667c7c344eb0d2
Source dataset
uspto-grants-1996_06
Patent number
US05527792

Reaction notes

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