Butylamine → (2R, 4S, 5S)-5(t-Butoxycarbonyl)amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamide

HRID 1768851Notes

Reaction equation

HRID 1768851 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].[CH2:24]([NH2:28])[CH2:25][CH2:26][CH3:27]>>[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:28][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 11023821(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 57144369(2R, 4S, 5S)-5(t-Butoxycarbonyl)amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamide

Procedure

A mixture of 0.4 g (1.23 mmole) of (3R, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 2) and 6 ml of butylamine was heated under reflux for 3.0 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 ethyl acetate as the eluent) to afford 0.48 g of the title compound as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.0 hours
  3. concentrationAt the end of this time, the reaction mixture was concentrated by distillation under reduced pressure
  4. customafter which the residue was purified by column chromatography through silica gel (

Sources & evidence

ORD record
ord-aeb24a76407c48bd8777a036ecca10b0
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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