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

HRID 1768863Notes

Reaction equation

HRID 1768863 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]([NH2:26])[CH3:25]>>[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:26][CH2:24][CH3:25])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 11023821(3R, 5S)-5-[(1S)-1-(t-Butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 15045757(2R, 4S, 5S)-5-(t-Butoxycarbonyl)amino-6-cyclohexyl-N-ethyl-4-hydroxy-2-methylhexanamide

Procedure

A solution of 325 mg (1.0 mmole) of (3R, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 2) in 10 ml of a 23% by volume methanolic solution of ethylamine was allowed to stand at room temperature for 3 hours and 55 minutes, after which the solvent was removed by distillation under reduced pressure. The residue was then recrystallizated from diisopropyl ether, to afford 321 mg of the title compound as white crystals, melting at 126°-127° C.

Workup

  1. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1138aa7851ec4715b04e3fc804589675
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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