[1-(4'-{4-[(E)-4-(4-Benzyl-phenyl)-1-hydroxy-but-3-enyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester → [1-(4'-{4-[4-(4-Benzyl-phenyl)-1-hydroxy-butyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester

HRID 1183330Notes

Reaction equation

HRID 1183330 reaction equation
[CH2:1]([O:3][C:4](=[O:45])[CH2:5][C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:44])[CH2:28]/[CH:29]=[CH:30]/[C:31]4[CH:36]=[CH:35][C:34]([CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:45])[CH2:5][C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:44])[CH2:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([CH2:37][C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 66581235[1-(4'-{4-[(E)-4-(4-Benzyl-phenyl)-1-hydroxy-but-3-enyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester

Product 1

HCID 66577652[1-(4'-{4-[4-(4-Benzyl-phenyl)-1-hydroxy-butyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[1-(4′-{4-[(E)-4-(4-Benzyl-phenyl)-1-hydroxy-but-3-enyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester (0.203 g, 0.340 mmol) was dissolved in EtOH and palladium on carbon (0.020 g, 10% wt., wet: 50% w/w H2O) was added. The reaction was stirred under H2 (g) atmosphere overnight then filtered through Celite to afford the title compound in EtOH solution, which was brought to the next step without further purification.

Workup

  1. filtrationthen filtered through Celite

Sources & evidence

ORD record
ord-6ce1e928f1c84a6db52c566d44272fb6
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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