HCID 15481806, compound → GI254023X
Reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C@H:3]([NH:8][C:9](=[O:32])[C@H:10]([CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:11]([N:13]([CH:21]=[O:22])[O:14]C1CCCCO1)[CH3:12])[C:4](=[O:7])[NH:5][CH3:6]>C(O)(=O)C.O>[CH3:33][C:2]([CH3:1])([CH3:34])[C@H:3]([NH:8][C:9](=[O:32])[C@H:10]([CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:11]([N:13]([CH:21]=[O:22])[OH:14])[CH3:12])[C:4](=[O:7])[NH:5][CH3:6]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2R,3S)-3-(Formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide (3.0 g, 6.32 mmol) in acetic acid-water (4:1, 10 mL) is heated to 50° C. for 16 h. The reaction mixture is concentrated, then dissolved in toluene and concentrated in vacuo. The procedure is repeated once again to afford the crude product which is triturated from hot dichloromethane-diethyl ether to provide (2R,3S)-3-(Formylhydroxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide as a white solid (2.3 g, 93% yield).