Methylamine → (2S, 4S, 5S)-5-(t-Butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamide

HRID 1768848Notes

Reaction equation

HRID 1768848 reaction equation
[CH3:1][NH2:2].[C:3]([O:7][C:8]([NH:10][C@H:11]([C@H:19]1[O:23][C:22](=[O:24])[C@H:21]([CH:25]([CH3:27])[CH3:26])[CH2:20]1)[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@@H:19]([OH:23])[CH2:20][C@@H:21]([CH:25]([CH3:27])[CH3:26])[C:22]([NH:2][CH3:1])=[O:24])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14217048(3S, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one

Product 1

HCID 14483185(2S, 4S, 5S)-5-(t-Butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamideYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Gaseous methylamine was introduced into a solution of 1.33 g (3.76 mmole) of (3S, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one (prepared as described in Preparation 1) in 10 ml of methanol to ensure saturation, whilst ice-cooling. The reaction vessel was then stoppered tightly and allowed to stand overnight. At the end of this time, the solvent was removed by distillation under reduced pressure and the residue was recrystallized from hexane to afford 1.32 g (yield 91%) of the title compound as white crystals, melting at 154°-157° C.

Workup

  1. temperaturewhilst ice-cooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-7c4b3b36fe814cd4af3a11878cc1d9fb
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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