Butylamine → (2S, 4S, 5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-butylhexanamide

HRID 1768849Notes

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]([CH:23]([CH3:25])[CH3:24])[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].[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>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]([CH:23]([CH3:24])[CH3:25])[C:20]([NH:30][CH2:26][CH2:27][CH2:28][CH3:29])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 890 mg (2.52 mmole) of (3S, 5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one (prepared as described in Preparation 1) and 2.5 ml (25.3 mmole) of butylamine was heated at 100° C. for 4 hours. At the end of this time, an excess of the butylamine was removed by distillation under reduced pressure, and the resulting residue was purified by medium pressure column chromatography through silica gel (using a 20:1 by volume mixture of methylene chloride and methanol as the eluent), followed by recrystallization from diisopropyl ether, to afford 1.05 g (yield 98%) of the title compound as white crystals, melting at 115°-118° C. [α]D20 =-34.9° (c=1, methanol).

Workup

customAt the end of this time, an excess of the butylamine was removed by distillation under reduced pressure
customthe resulting residue was purified by medium pressure column chromatography through silica gel (
additionby volume mixture of methylene chloride and methanol as the eluent),
customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record: ord-fae4522dbaac4db8b6b047f596b790b0
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05378689

Reaction notes

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