methyl (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789349Notes

Reaction equation

HRID 1789349 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=S.C[O:32]C1C=CC([C@H]2O[C@@H]2C(OC)=O)=CC=1>C(O)C>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:32]

Participants

4

Reactant 2

HCID 719742methyl (2S,3R)-3-(4-methoxyphenyl)oxirane-2-carboxylate2×HCID 13767979(+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide

Product 1

HCID 13767927N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

480 mg of (+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide and 339 mg of methyl trans-3-(4-methoxyphenyl)glycidate are dissolved in 40 ml of ethanol, and the solution is refluxed for 11 hours under heating. 339 mg of methyl trans-3-(4-methoxyphenyl)glycidate are added to the mixture, and the mixture is further refluxed for 3 hours. The mixture is concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:ethanol=40:1), and the resultant product is recrystallized from a mixture of ethyl acetate and n-hexane. 350 mg of (+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained. Yield: 75.7%.

Workup

  1. temperaturethe solution is refluxed for 11 hours
  2. temperatureunder heating
  3. temperaturethe mixture is further refluxed for 3 hours
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customto remove solvent
  6. customThe residue is purified by silica gel chromatography (solvent, chloroform:ethanol=40:1)
  7. customthe resultant product is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-f3e68c165c3c48f0b4660070a759059b
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

Loading…