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

HRID 1768861Notes

Reaction equation

HRID 1768861 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])[CH:25]([CH3:27])[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:28][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 11023821(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 15045755(2R, 4S, 5S)-5-(t-Butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-N-isobutyl-2-methylhexanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 290 mg (0.93 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 isobutylamine, 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 340 mg of the title compound as colorless crystals, melting at 125°-126° C.

Workup

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

Sources & evidence

ORD record
ord-3135daf03cb84048a57f502366deb3ed
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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