HCID 178485760, compound → HCID 178485759, compound

HRID 1655723Notes

Reaction equation

HRID 1655723 reaction equation
C([O:8][C:9](=[O:36])[C@H:10]([CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)[N:11]([C:13](=[O:29])[C@H:14]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])C1C=CC=CC=1>[Pd]>[CH2:22]([C@H:14]([CH2:15][C:16](=[O:21])[C:17]([CH3:19])([CH3:18])[CH3:20])[C:13]([N:11]([CH3:12])[C@H:10]([C:9]([OH:36])=[O:8])[CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1)=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 178485760HCID 178485760, compound

Product 1

HCID 178485759HCID 178485759, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

195 mg of N-[(R)-2-benzyl-5,5-dimethyl-4-oxohexanoyl]-N-methyl-L-histidine benzyl ester were hydrogenated in the presence of 25 mg of palladium-on-carbon (5%) for 2 hours and the N-[(R)-2-benzyl-5,5-dimethyl-4-oxohexanoyl]-N-methyl-L-histidine obtained was reacted in the usual manner with (αS,βS)-β-amino-α-[(S)-2-isopropyl-3-butenyl]cyclohexanepropanol. Chromatographic purification of the crude product obtained on silica gel with a 140:10:0.1 mixture of methylene chloride, methanol and ammonia yielded N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]-α-[(R)-2-benzyl-N,5,5-trimethyl-4-oxohexanamido]imidazole-4-propionamide as a thin-layer chromatographically uniform substance, MS: 635 (M+H)+.

Sources & evidence

ORD record
ord-34263ada73324805abfc73b2ee1f7776
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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