Water → 4-(3-Bromobenzyl)-5-methyloxazole-2-carboxylic acid

HRID 517547Notes

Reaction equation

HRID 517547 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[N:7]=[C:8]([C:12]([O:14]CC)=[O:13])[O:9][C:10]=1[CH3:11].[OH-].[Na+].O>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[N:7]=[C:8]([C:12]([OH:14])=[O:13])[O:9][C:10]=1[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86711486Ethyl 4-(3-bromobenzyl)-5-methyloxazole-2-carboxylate

Product 1

HCID 867114884-(3-Bromobenzyl)-5-methyloxazole-2-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 4-(3-bromobenzyl)-5-methyloxazole-2-carboxylate (500 mg, 1.5 mmol) and 2 N NaOH (2 mL, 4 mmol) in EtOH (6 mL)/H2O (2 mL) was stirred at 0° C. for 2 h. The mixture was neutralized with aqueous critic acid (10%), concentrated and purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA) to afford 4-(3-bromobenzyl)-5-methyloxazole-2-carboxylic acid as a yellow oil (320 mg, 65%). MS (ES+) C12H10BrNO3 requires: 295, 297, found: 296 [M+H]+, 298 [M+2+H]+(1:1).

Workup

  1. concentrationconcentrated
  2. custompurified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA)

Sources & evidence

ORD record
ord-21275fab8b0343d39a866ce503144df5
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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