(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one → (2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-N-hexyl-4-hydroxy-2-methylhexanamide
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH3:23])[CH2:18]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(N)CCCCC>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH3:23])[C:20]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
A mixture of 450 mg (1.38 mmole) of (3R, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 2) and 10 ml of hexylamine was heated under reflux for 2.2 hours, whilst stirring. At the end of this time, the reaction mixture was concentrated by distillation under reduced pressure, after which the residue was purified by column chromatography through silica gel (using a 1:2 by volume mixture of cyclohexane and ethyl acetate as the eluent) to afford 443 mg of the title compound as white crystals.
Workup
- temperaturewas heated
- temperatureunder reflux for 2.2 hours
- concentrationAt the end of this time, the reaction mixture was concentrated by distillation under reduced pressure
- customafter which the residue was purified by column chromatography through silica gel (
- additionby volume mixture of cyclohexane and ethyl acetate as the eluent)
Sources & evidence
- ORD record
- ord-ffd2f40b4fc94f4a8029f4331dccbf35
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378689
Reaction notes
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