Water → HCID 178476516, compound

HRID 2294701Notes

Reaction equation

HRID 2294701 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:16][C:17]([C@@H:19]([NH:26][C:27]([C@H:29]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:30][S:31]([CH2:34][C:35]([NH:38]C(=O)OCC2C=CC=CC=2)([CH3:37])[CH3:36])(=[O:33])=[O:32])=[O:28])[CH2:20][C:21]2[N:22]=[CH:23][NH:24][CH:25]=2)=[O:18])[C@@H:9]([OH:15])[C@H:10]([CH:12]2[CH2:14][CH2:13]2)[OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:56]>C(O)(=O)C.[Pd]>[C:10]([OH:11])(=[O:56])[CH3:9].[C:10]([OH:11])(=[O:56])[CH3:9].[NH2:38][C:35]([CH3:37])([CH3:36])[CH2:34][S:31]([CH2:30][C@@H:29]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:27]([NH:26][C@@H:19]([CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[C:17]([NH:16][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:9]([OH:15])[C@H:10]([CH:12]1[CH2:14][CH2:13]1)[OH:11])=[O:18])=[O:28])(=[O:32])=[O:33]

Participants

5

Reactant 2

HCID 962WaterHCID 178455613HCID 178455613, compound

Product 1

HCID 178476516HCID 178476516, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 300 mg (0.38 mmol) of benzyl [2-[[(S)-2-[[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]-3-phenylpropyl]sulphonyl]-1,1-dimethylethyl]carbamate and 30 mg of palladium/carbon (10%) in 8 ml of acetic acid is hydrogenated at room temperature for 3 hours. Thereafter, the catalyst is filtered off, the reaction solution is evaporated and the residue obtained is lyophilized from water. There are obtained 240 mg of (S)-α-[(S)-α-[[(2-amino-2-methylpropyl)sulphonyl]methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide diacetate as a colourless, amorphous powder; MS: 646 (M+H)+.

Workup

  1. filtrationThereafter, the catalyst is filtered off
  2. customthe reaction solution is evaporated
  3. customthe residue obtained

Sources & evidence

ORD record
ord-c199b0c63c814abfbf553da5f34d4a37
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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