Ethylamine → (2S, 4S, 5S)-5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-ethylhexanamide

HRID 2380132Notes

Reaction equation

HRID 2380132 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[CH2:19][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].[CH2:23]([NH2:25])[CH3:24]>CO.C(OCC)C>[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]([C:1]([OH:5])([CH3:3])[CH3:2])[C:20]([NH:25][CH2:23][CH3:24])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 10946873(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

Product 1

HCID 14989082(2S, 4S, 5S)-5-(t-butoxycarbonylamino)-6-cyclohexyl-4-hydroxy-2-(1-hydroxy-1-methylethyl)-N-ethylhexanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 400 mg (1.08 mmoles) of (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one (prepared as described in Preparation 5) in 20 ml of methanol was saturated with ethylamine. After it had been allowed to stand at room temperature overnight, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue obtained, as an oily substance was dissolved in warm diethyl ether. The solution was then allowed to stand, and the needle-like crystals which deposited were collected by filtration, to give 317 mg of the title compound, melting at 155°-157° C.

Workup

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe residue obtained, as an oily substance
  3. filtrationthe needle-like crystals which deposited were collected by filtration

Sources & evidence

ORD record
ord-e3a9f756280147a1a24d7a5ba5c3b23b
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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