Potassium Carbonate → Methyl 3-[(2-amino-1,3-thiazol-5-yl)sulfanyl]propanoate

HRID 2279274Notes

Reaction equation

HRID 2279274 reaction equation
C([O-])([O-])=O.[K+].[K+].Br.Br[C:9]1[S:13][C:12]([NH2:14])=[N:11][CH:10]=1.[SH:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C.O>[NH2:14][C:12]1[S:13][C:9]([S:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:10][N:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18050Methyl 3-mercaptopropionateHCID 27238485-Bromothiazol-2-amine monohydrobromide

Product 1

HCID 71424317Methyl 3-[(2-amino-1,3-thiazol-5-yl)sulfanyl]propanoateYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

K2CO3 (14.0 g, 100 mmol) was added to a solution of 5-bromothiazol-2-amine hydrobromide (13.0 g, 50 mmol) in 90 ml of dry DMF at 0° C. under nitrogen. After 0.5 h, methyl 3-sulfanylpropanoate (6.0 g, 50 mmol) was added dropwise to the mixture over the course of 30 min and stirred at ambient temperature for 48 h. Then the mixture was diluted with 500 ml of water and extracted with TBME. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography on silica gel to give the title compound (7.6 g, 70% yield) 1H NMR (400 Mz, CDCl3) δ2.53 (t, 2H), 2.75 (t, 2H), 3.58 (s, 3H), 7.25 (s, 1H).

Workup

  1. extractionextracted with TBME
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-689bd16c299f4cfebdc7e7d42cdc9808
Source dataset
uspto-grants-2015_09
Patent number
US09133218B2

Reaction notes

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