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

HRID 1266771Notes

Reaction equation

Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=O.C(C([O:22][CH2:23][C:24]([NH2:26])=[S:25])=O)(C)(C)C>CCO>[OH:22][CH2:23][C:24]1[S:25][C:2]([CH3:15])=[C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])[N:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 3-(2-bromo-propionyl)-benzoate (2.7 g) and 2-(tert.-butyl-carbonyloxy)thioacetamide (2.1 g) in EtOH (20 mL) was heated at reflux for 8 h. The mixture was partitioned between H2O and AcOEt. The organic layer was dried and evaporated. The residue was dissolved in MeOH (20 ml), NaOMe (0.54 g) was added, and the mixture was heated to 60° C. for 1 h. The mixture was diluted with AcOEt and then washed with 3N HCl and brine. The organic layer was dried and evaporated and the residue was crystallized from AcOEt to give methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate (1.17 g) as white solid.

Workup

temperatureat reflux for 8 h
customThe mixture was partitioned between H2O and AcOEt
customThe organic layer was dried
customevaporated
dissolutionThe residue was dissolved in MeOH (20 ml)
additionNaOMe (0.54 g) was added
additionThe mixture was diluted with AcOEt
washwashed with 3N HCl and brine
customThe organic layer was dried
customevaporated
customthe residue was crystallized from AcOEt

Sources & evidence

ORD record: ord-780c0c6dc70f4ae28f07998a4264b8ef
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548495B2

Reaction notes

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