HCID 178456025, compound → HCID 178455997, compound

HRID 1655719Notes

Reaction equation

HRID 1655719 reaction equation
C([O:8][NH:9][C:10]([CH:12]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:13]([NH:15][C@@H:16]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:17]([NH:19][C@@H:20]([CH:30]1CCCCC1)[C@@H:21]([OH:29])[CH2:22][C@@H:23]([CH:26]([CH3:28])[CH3:27])[CH:24]=[CH2:25])=[O:18])=[O:14])=[O:11])C1C=CC=CC=1>[Pd].CO>[CH:43]1([CH2:30][C@H:20]([NH:19][C:17](=[O:18])[C@@H:16]([NH:15][C:13](=[O:14])[CH:12]([C:10](=[O:11])[NH:9][OH:8])[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:36][C:37]2[N:38]=[CH:39][NH:40][CH:41]=2)[C@@H:21]([OH:29])[CH2:22][C@H:23]([CH2:24][CH3:25])[CH:26]([CH3:28])[CH3:27])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

4

Reactant 1

HCID 178456025HCID 178456025, compound

Product 1

HCID 178455997HCID 178455997, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

150 mg of (S)-α-[(RS)-α-[(benzyloxy)carbamoyl]-hydrocinnamamido]-N-[(1S,2S,4S)-1-cyclohexyl-2-hydroxy 4-isopropyl-5-hexenyl]imidazole-4-propionamide were hydrogenated in the presence of 5% palladium on carbon in methanol for 3 hours. After completion of hydrogen uptake, the catalyst was filtered and the filtrate was evaporated. Recrystallization of the residue from methanol/methylene chloride/ether yielded (S)-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-4-ethyl-2-hydroxy-5-methylhexyl]-α-[(RS)-α-(hydroxycarbamoyl)hydrocinnamamido]imidazole-4-propionamide as white crystals of melting point 123°.

Workup

  1. filtrationAfter completion of hydrogen uptake, the catalyst was filtered
  2. customthe filtrate was evaporated
  3. customRecrystallization of the residue from methanol/methylene chloride/ether

Sources & evidence

ORD record
ord-8c46f3b37f864252b098f828dfa612b6
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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