(S)-2-[BENZYL-(3-CHLORO-2-HYDROXY-PROPYL)-AMINO]-N-(4-BENZYLOXY-PHENYL)-ACETAMIDE synthesis
- Product Name:(S)-2-[BENZYL-(3-CHLORO-2-HYDROXY-PROPYL)-AMINO]-N-(4-BENZYLOXY-PHENYL)-ACETAMIDE
- CAS Number:777934-41-5
- Molecular formula:C25H27ClN2O3
- Molecular Weight:438.95
Yield:777934-41-5 100%
Reaction Conditions:
with magnesium sulfate in methanol;dichloromethane at 35; for 72 h;
Steps:
A.iii; 4.iii Scheme 4
2-BENZYLAMINO-N- (4-BENZYLOXYPHENYL)-ACETAMIDE (63 g, 0.18 mol) was dissolved in methanol (1L). Magnesium sulfate was added (26 g) followed by dichloromethane (0.35 L). S-Epichlorohydrin (42.07 g, 0.45 mol) was added via syringe. Once addition was complete the reaction mixture was heated to 35°C and stirred for 72 h. The reaction mixture was filtered through a pad of celite. The pad was washed with ethyl acetate and organic fractions combined. The organic layer was concentrated under reduced pressure to yield 79.8 g (100%) of 2-{benzyl-[(2S)-3-chloro-2- HYDROXYPROPYL]-AMINO}-N- (4-BENZYLOXYPHENYL)-ACETAMIDE as a dark oil. MS: M/Z 439. 1 (M+L).
References:
WO2004/89915,2004,A1 Location in patent:Page 59; 61