2-Methylbutylamine, (S)- → (2S, 4S, 5S)-5-(t-Butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]-hexanamide

HRID 2380119Notes

Reaction equation

HRID 2380119 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]([C:23]([OH:26])([CH3:25])[CH3:24])[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].[CH3:27][C@@H:28]([CH2:31][CH3:32])[CH2:29][NH2:30]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([C:23]([OH:26])([CH3:25])[CH3:24])[C:20]([NH:30][CH2:29][C@@H:28]([CH3:27])[CH2:31][CH3:32])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27242722-Methylbutylamine, (S)-HCID 14483171(3S, 5S)-5-[(1S)-1-(N-t-Butoxycarbonylamino)-2-cyclohexylethyl]-3-(1-hydroxy-1-methylethyl)dihydrofuran-2(3H)-one

Product 1

HCID 14989049(2S, 4S, 5S)-5-(t-Butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-[2(S)-methylbutyl]-hexanamideYield 92.5%

Procedure

A solution of 500 mg (1.35 mmoles) of (3S, 5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]-3-(1-hydroxy-1-methylethyl)dihydrofuran-2(3H)-one (prepared as described in Preparation 6) in 1.00 g (11.5 mmoles) of 2(S)-methylbutylamine was stirred at 100° C. for 4 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 20:1 by volume mixture of methylene chloride and methanol as eluent), to give 570 mg (yield 92%) of the title compound as white crystals, melting at 64°-67° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe residue was purified by medium pressure silica gel column chromatography (
  3. additionby volume mixture of methylene chloride and methanol as eluent),

Sources & evidence

ORD record
ord-cea96743ffb04e68b4449463e614e297
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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