2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate

HRID 1265624Notes

Reaction equation

HRID 1265624 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH3:12])[CH:5]=1.C(C([O:22][CH2:23][C:24]([NH2:26])=[S:25])=O)(C)(C)C>CCO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:26]=[C:24]([CH2:23][OH:22])[S:25][C:11]=2[CH3:12])[CH:5]=1

Participants

4

Reactant 2

HCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoateHCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Product 1

HCID 18548740Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoateYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of rac-3-(2-bromo-propionyl)-benzoic acid methyl ester (2.71 g) and 2-(tert.-butylcarbonyloxy)thioacetamide (2.1 g) in EtOH (20 mL) was heated at reflux for 6 h. The mixture was partitioned between AcOEt and brine, and the organic layer was dried and evaporated. A solution of the residual oil and NaOMe (0.54 g) in MeOH (20 mL) was stirred at 60° C. for 1 h. The solution was diluted with AcOEt, washed with 1N HCl and brine, dried and evaporated to give 3-(2-hydroxymethyl-5-methyl-thiazol-4-yl)-benzoic acid methyl ester (1.17 g) as white crystals, MS (ISP) 264.1 [(M+H)+].

Workup

  1. temperatureat reflux for 6 h
  2. customThe mixture was partitioned between AcOEt and brine
  3. customthe organic layer was dried
  4. customevaporated
  5. additionThe solution was diluted with AcOEt
  6. washwashed with 1N HCl and brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-85fb36809621444e990fd10b5ec1b052
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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