Water → 5-{(1R)-4-Cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamide Monohydrate

HRID 1279766Notes

Reaction equation

HRID 1279766 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]([NH2:23])=[O:22])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O>O1CCCC1>[OH2:13].[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]([NH2:23])=[O:22])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 962WaterHCID 9818682(R)-5-(6-cyclohexyl-1-(hydroxyamino)-1-oxohexan-3-yl)-1,2,4-oxadiazole-3-carboxamide

Product 1

HCID 865837005-{(1R)-4-Cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamide MonohydrateYield 164.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamide (1.58 Kg, 4.86 mol) in tetrahydrofuran (15 litres) was heated to 40° C. and demineralised water (26 litres) was added to give a hazy solution. The mixture was allowed to cool to ambient temperature where it was stirred for 24 hours. The mixture was cooled to 5° C. and stirred for 1 hour. The precipitate was collected by filtration and dried in vacuo (38° C., 100 mbar) to afford the title compound as a colourless solid (1.37 Kg).

Workup

  1. customto give a hazy solution
  2. temperatureThe mixture was cooled to 5° C.
  3. stirringstirred for 1 hour
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo (38° C., 100 mbar)

Sources & evidence

ORD record
ord-9084dd2e9ed547d5b91b381857404115
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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