Propylamine → (2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

HRID 1768862Notes

Reaction equation

HRID 1768862 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]([NH2:27])[CH2:25][CH3:26]>CO>[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:27][CH2:24][CH2:25][CH3:26])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 11023821(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 57031843(2R, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 293 mg (0.9 mmole) of (3R, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 2) in 3 ml of methanol was mixed with 3 ml of propylamine, whilst ice-cooling, and the mixture was allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was concentrated by distillation under reduced pressure, and the residue was triturated with hexane to afford 315 mg of the title compound as white crystals, melting at 115°-116° C.

Workup

  1. temperaturecooling
  2. concentrationAt the end of this time, the reaction mixture was concentrated by distillation under reduced pressure
  3. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-deeb7d9f122f444cb6773f7862010cef
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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