Potassium Carbonate → Methyl-2-(3-(4-methoxybenzyloxycarbonyl)propylthio)-4-methyl-1,3-thiazol-5-ylacetate

HRID 34673Notes

Reaction equation

HRID 34673 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:7])[N:6]=1.Cl[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:4]1[S:3][C:2]([S:1][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[O:18])=[N:6][C:5]=1[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124256804-Methoxybenzyl 4-chlorobutyrateHCID 178499653HCID 178499653, compound

Product 1

HCID 131715689Methyl-2-(3-(4-methoxybenzyloxycarbonyl)propylthio)-4-methyl-1,3-thiazol-5-ylacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.2 g of methyl 2-mercapto-4-methyl-1,3-thiazol-5-yl-acetate are dissolved in 200 ml of acetone, and the solution is vigorously stirred with 12.1 g of 4-methoxybenzyl 4-chlorobutyrate in the presence of 13.0 g of powdered, dry potassium carbonate (potash) while maintaining the ambient temperature. After filtration, acetone is removed in vacuo, and the residue is purified by column chromatography (SiO2, ethyl acetate/cyclohexane 1:1). ##STR8##

Workup

  1. filtrationAfter filtration, acetone
  2. customis removed in vacuo
  3. customthe residue is purified by column chromatography (SiO2, ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-a514ed01ea4c4cae9f6811e857b957ec
Source dataset
uspto-grants-1988_08
Patent number
US04762848

Reaction notes

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