Ammonia → tert-Butyl (3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl)-6-phenylhexanoate

HRID 1279816Notes

Reaction equation

HRID 1279816 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].[NH3:29]>C(O)C>[NH2:29][C:23]([C:20]1[N:19]=[C:18]([C@H:8]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])[O:22][N:21]=1)=[O:24]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 86583702tert-Butyl (3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl)-6-phenylhexanoate

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 3) (400 mg, 1.01 mmol) in ethanol saturated with ammonia gas (20 ml) was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a gradient system of hexane:ethyl acetate (90:10) gradually changing to hexane: ethyl acetate (60:40) to afford the title compound as a white solid ( 260 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with a gradient system of hexane:ethyl acetate (90:10)

Sources & evidence

ORD record
ord-f632fa85231e43ab9342d27dd4c227fe
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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