HCID 178455611, compound → HCID 178455610, compound

HRID 2294735Notes

Reaction equation

HRID 2294735 reaction equation
[N:1]([C@@H:4]([CH:44]1[CH2:46][CH2:45]1)[C@H:5]([OH:43])[C@@H:6]([NH:14][C:15](=[O:42])[C@@H:16]([NH:23][C:24](=[O:41])[C@@H:25]([CH2:33][S:34]([C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:36])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]([CH:44]1[CH2:46][CH2:45]1)[C@@H:5]([OH:43])[C@@H:6]([NH:14][C:15](=[O:42])[C@@H:16]([NH:23][C:24](=[O:41])[C@@H:25]([CH2:33][S:34]([C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:36])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 178455611HCID 178455611, compound

Product 1

HCID 178455610HCID 178455610, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 60 mg (0.09 mmol) of (S)-N-[(1S,2R,3S)-3-azido-1-(cyclohexylmethyl)-3-cyclopropyl-2-hydroxypropyl]-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionamide and 20 mg of palladium/carbon (5%) in 15 ml of methanol is hydrogenated at room temperature for 4 hours. After filtering off the catalyst the solvent is evaporated under reduced pressure. For purification, the crude product (40 mg) is chromatographed on 10 g of silica gel using a 80:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 35 mg of (S)-N-[(1S,2R,3S)-3-amino-1-(cyclohexylmethyl)-3-cyclopropyl-2-hydroxypropyl]-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionamide as a colourless solid; MS: 630 (M+H)+.

Workup

  1. filtrationAfter filtering off the catalyst the solvent
  2. customis evaporated under reduced pressure
  3. customFor purification
  4. customthe crude product (40 mg) is chromatographed on 10 g of silica gel using
  5. additiona 80:10:1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-981b5c4c2358473a84fc3d944b44ae80
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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