(2S)-2-(phenoxymethyl)oxirane → (S)-2-(2-benzylamino-4-thiazolyl)-4'-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]acetanilide
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:26])[CH2:12][C:13]2[N:14]=[C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:16][CH:17]=2)=[CH:6][CH:5]=1.[O:27]([CH2:34][C@@H:35]1[CH2:37][O:36]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(O)C>[CH2:19]([NH:18][C:15]1[S:16][CH:17]=[C:13]([CH2:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][CH2:37][C@H:35]([OH:36])[CH2:34][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:5][CH:6]=2)=[O:26])[N:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 670 mg of N-[4-(2-aminoethyl)phenyl]-2-(2-benzylaminothiazol-4-yl)acetamide and 300 mg of (S)-2-[(phenoxy)methyl]oxirane in 20 ml of 2-propanol was heated under refluxing for three hours. The solvent was evaporated off in vacuo and the residue was purified by means of silica gel column chromatography (eluate: chloroform/methanol=10/1). The resulting solid was recrystallized from methanol to obtain 250 mg of (S)-2-(2-benzylamino-4-thiazolyl)-4′-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]acetanilide.
Workup
- temperatureunder refluxing for three hours
- customThe solvent was evaporated off in vacuo
- customthe residue was purified by means of silica gel column chromatography (eluate: chloroform/methanol=10/1)
- customThe resulting solid was recrystallized from methanol
Sources & evidence
- ORD record
- ord-d2427482603442eeb6a66e68ee18061c
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06177454B1
Reaction notes
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