Hydrochloric Acid → 4-(3-Bromobenzyl)-5-methylthiazole-2-carboxylic acid

HRID 517553Notes

Reaction equation

HRID 517553 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])[S:9][C:10]=1[CH3:11].O[Li].O.Cl>C1COCC1.CO.O.CCOC(C)=O.O>[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])[S:9][C:10]=1[CH3:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86711493Ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate

Product 1

HCID 867114944-(3-Bromobenzyl)-5-methylthiazole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of ethyl 4-(3-bromobenzyl)-5-methylthiazole-2-carboxylate (20 mg, 0.06 mmol) was treated with LiOH.H2O (7.5 mg, 0.18 mmol) in 2 mL of THF/MeOH/H2O (2:1:1) and stirred at RT for 2 h. The reaction was diluted with EtOAc and H2O and then acidified by 6N HCl. The organic layer was separated and concentrated to give a crude which was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated
  3. customto give a crude which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-1bcc059b980245e1a5ec5e309f855f0a
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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