Hydrazine hydrate (1:1) → HCID 60077680, compound

HRID 1350223Notes

Reaction equation

HRID 1350223 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23](OCC)=[O:24])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[NH2:29][NH2:30].O>CCO>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([NH:29][NH2:30])=[O:24])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 60077680HCID 60077680, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazole-3-carboxylate (preparation 170) (1.14 g, 2.89 mmol) in EtOH (20 ml) was treated with NH2NH2.H2O (280 μl, 5.78 mmol) and stirred at room temperature for 45 minutes. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and H2O/brine. The organic solvent was removed under reduced pressure to afford the title compound (1.06 g, 90%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc and H2O/brine
  3. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b7d97036f49c46f0a787b5f6b5031b2e
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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