Methylamine → (2R, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2, N-dimethylhexanamide

HRID 1768867Notes

Reaction equation

HRID 1768867 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([NH:18][C@H:19]([C@H:27]1[O:31][C:30](=[O:32])[C@H:29]([CH3:33])[CH2:28]1)[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][NH2:35]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C@@H:27]([OH:31])[CH2:28][C@@H:29]([CH3:33])[C:30]([NH:35][CH3:34])=[O:32])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86748373(3R, 5S)-5-{(1S)-1-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-2-cyclohexylethyl}-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 15045762(2R, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2, N-dimethylhexanamide

Procedure

A solution of 500 mg (1.04 mmole) of (3R, 5S)-5-{(1S)-1-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-2-cyclohexylethyl}-3-methyldihydrofuran-2(3H)-one (prepared as described in Preparation 25) in 2.5 ml of a 40% by volume methanolic solution of methylamine was allowed to stand at room temperature for 1 hour. At the end of this time, any excess of the methylamine and the methanol were removed by distillation under reduced pressure. The resulting residue was recrystallized from ethyl acetate to afford 405 mg of the title compound as white crystals, melting at 158°-160° C.

Workup

  1. customAt the end of this time, any excess of the methylamine and the methanol were removed by distillation under reduced pressure
  2. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a5528ebced464fc59ca526d6914430c7
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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