Bromopyruvic Acid → HCID 66728004, compound

HRID 1370707Notes

Reaction equation

HRID 1370707 reaction equation
[C:1]([NH:18][C:19]([NH2:21])=[S:20])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].Br[CH2:23][C:24](=O)[C:25]([OH:27])=[O:26]>O1CCOCC1>[C:1]([N:18]1[C:24]([C:25]([OH:27])=[O:26])=[CH:23][S:20][CH:19]1[NH2:21])([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2]

Participants

4

Reactant 2

HCID 70684Bromopyruvic AcidHCID 11472050HCID 11472050, compound

Product 1

HCID 66728004HCID 66728004, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-Fmoc-thiourea (5.96 g, 20 mmol) in dioxane (40 mL) was treated with bromopyruvic acid (3.34 g, 20 mmol). The reaction mixture was refluxed for 1 h, then the precipitated solids were recovered by filtration and washed with diethyl ether (3×20 mL) to afford N-Fmoc-2-aminothiazole-4-carboxylic acid (7.1 g, 97%) as a white solid: EI-HRMS m/e calcd for C19H14N2O4S (M+) 366.0674, found 366.0679.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationthe precipitated solids were recovered by filtration
  3. washwashed with diethyl ether (3×20 mL)

Sources & evidence

ORD record
ord-26f297d4c7334fe08601fb04a30dbe99
Source dataset
uspto-grants-2003_06
Patent number
US06583288B2

Reaction notes

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