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

HRID 1265627Notes

Reaction equation

HRID 1265627 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH2:12]CC)[CH:5]=1.C(C([O:24][CH2:25][C:26]([NH2:28])=[S:27])=O)(C)(C)C>CCO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:28]=[C:26]([CH2:25][OH:24])[S:27][C:11]=2[CH3:12])[CH:5]=1

Participants

4

Reactant 2

HCID 27821132-Amino-2-thioxoethyl 2,2-dimethylpropanoateHCID 87951238Rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester

Product 1

HCID 18548740Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoateYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A sample of rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester (0.60 g) and and 2-(tert.-butylcarbonyloxy)thioacetamide (0.36 g) in EtOH (4 mL) was heated at reflux for 5 h. The mixture was partitioned between AcOEt and 5% NaHCO3 solution, the organic layer was washed with brine, dried and evaporated. A solution of the residual oil and of NaOMe (0.13 g) in MeOH (10 mL) was stirred at 60° C. for 30 min. 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 (0.44 g) as an oil.

Workup

  1. temperatureat reflux for 5 h
  2. customThe mixture was partitioned between AcOEt and 5% NaHCO3 solution
  3. washthe organic layer was washed with brine
  4. customdried
  5. customevaporated
  6. additionThe solution was diluted with AcOEt
  7. washwashed with 1N HCl and brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-7877cd96d16d4d5b9c95c1b96a4aac7d
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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