(3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno[3,4-d]imidazol-4-ylidene pentanoic acid → (3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno-[3,4-d]-imidazol-4-yl pentanoic acid

HRID 373403Notes

Reaction equation

[C:1]1([C@H:7]([N:9]2[C@H:13]3[CH2:14][S:15][C:16](=[C:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=[O:19])[C@H:12]3[N:11]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]2=[O:31])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C)C.[Pd]>[C:1]1([C@H:7]([N:9]2[C@H:13]3[CH2:14][S:15][CH:16]([CH:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=[O:19])[C@H:12]3[N:11]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:10]2=[O:31])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 78.6 mg of (3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno-[3,4-d]-imidazol-4-ylidene pentanoic acid in 5 ml of isopropanol was placed in a 100-ml autoclave and 39 mg of palladium (5 percent) on carbon added. The autoclave was flushed twice with hydrogen and the mixture was stirred under 50 bars of hydrogen pressure at 50° C. for 24 hours. Then the catalyst was filtered off and the solvent evaporated off. The product, (3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno-[3,4-d]-imidazol-4-yl pentanoic acid, was obtained as a colorless oil in a yield of 56.1 mg (72 percent). Concerning the product:

Workup

additionadded
customThe autoclave was flushed twice with hydrogen
filtrationThen the catalyst was filtered off
customthe solvent evaporated off

Sources & evidence

ORD record: ord-20a0ccdfffc04a3d9954c5fe8657bc37
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162540

Reaction notes

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