HCID 178448268, compound → HCID 178448269, compound

HRID 847326Notes

Reaction equation

HRID 847326 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:30][C:31]([C@@H:33]([NH:40][C:41]([C@@H:43]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[CH2:34][C:35]2[N:36]=[CH:37][NH:38][CH:39]=2)=[O:32])[C@@H:9]([OH:29])[CH2:10][C@@H:11]([CH:26]([CH3:28])[CH3:27])[CH2:12]/[CH:13]=[CH:14]/[C:15](=[O:25])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:7][C@H:8]([NH:30][C:31]([C@@H:33]([NH:40][C:41]([C@@H:43]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:55])([CH3:57])[CH3:56])[CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:42])[CH2:34][C:35]2[N:36]=[CH:37][NH:38][CH:39]=2)=[O:32])[C@@H:9]([OH:29])[CH2:10][C@@H:11]([CH:26]([CH3:28])[CH3:27])[CH2:12][CH2:13][CH2:14][C:15](=[O:25])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 178448268HCID 178448268, compound

Product 1

HCID 178448269HCID 178448269, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

80 mg (0.10 mmol) of t-butyl [(S)-[[(S)-1-[[(1S,2S,4S,E)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-7-(phenethylcarbamoyl)-6-heptenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate are dissolved in 1 ml of methanol and, after the addition of 0.015 g of palladium on charcoal (5%), hydrogenated for 7 hours at room temperature and atmospheric pressure. After completion of the hydrogen uptake the catalyst is filtered off and the filtrate is evaporated under reduced pressure, whereby there are obtained 64 mg of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-7-(phenethylcarbamoyl)heptyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate as an amorphous solid, MS: 801 (M+H)+.

Workup

  1. filtrationAfter completion of the hydrogen uptake the catalyst is filtered off
  2. customthe filtrate is evaporated under reduced pressure, whereby there

Sources & evidence

ORD record
ord-b57ef3a264e543cabe12783a021b1828
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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