Methylamine → (2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2,N-dimethylhexanamide

HRID 1768850Notes

Reaction equation

HRID 1768850 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]([CH3:25])[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]([CH3:25])[C:22]([NH:2][CH3:1])=[O:24])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11023821(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 15045750(2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2,N-dimethylhexanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Gaseous methylamine was introduced into a solution of 0.2 g (0.615 mole) of (3R, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 2) in 6 ml of methanol for 3 minutes, after which the mixture was allowed to stand for 3 hours. The reaction mixture was then concentrated by distillation under reduced pressure, and the resulting residue was triturated with hexane to afford 0.23 g of the title compound as white crystals, melting at 144°-145° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by distillation under reduced pressure
  2. customthe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-a1a572b55c0e4f22ac136b3b372a9ceb
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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