Ethyl Acetate → 3-[(2S)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]-2-(t-butoxycarbonylamino)propoxy]-4-iodobenzonitrile

HRID 747763Notes

Reaction equation

HRID 747763 reaction equation
Cl[CH2:2][C@@H:3]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:4][C:5]1[CH:27]=[CH:26][C:8]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1.[OH:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[I:45])[C:40]#[N:41].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:10]([O:9][C:8]2[CH:26]=[CH:27][C:5]([CH2:4][C@H:3]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:2][O:36][C:37]3[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=3[I:45])[C:40]#[N:41])=[CH:6][CH:7]=2)[CH2:11][CH2:12]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 109446813-Hydroxy-4-iodobenzonitrileHCID 68834205HCID 68834205, compound

Product 1

HCID 688341513-[(2S)-3-[4-(1-benzyloxycarbonyl-4-piperidyloxy)phenyl]-2-(t-butoxycarbonylamino)propoxy]-4-iodobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

1.3 g (2.6 mmol) of benzyl 4-[4-[(2S)-3-chloro-2-(t-butoxycarbonylamino)propyl]phenoxy]piperidine-1-carboxylate, 686 mg (2.8 mmol) of 3-hydroxy-4-iodobenzonitrile and 390 mg (2.8 mmol) of potassium carbonate were dissolved in dimethylformamide. The solution was stirred at 65° C. for 4 days, and then treated with ethyl acetate as the extractant in an ordinary manner to obtain the title compound, which was then subjected to the subsequent reaction without further purification.

Sources & evidence

ORD record
ord-e8bd002c588e4ab39239b4734c6b053b
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…