HCID 178447297, compound → HCID 178447296, compound

HRID 1609214Notes

Reaction equation

HRID 1609214 reaction equation
C([O:8][C:9]([C@@H:11]([N:27]([C:46](=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[NH:45][N:44]=[N:43][N:42]=2)=[CH:31][CH:30]=1)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]C(OCC1C=CC=CC=1)=O)=[O:10])C1C=CC=CC=1>CO.[Pd]>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([N:27]([C:46](=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[NH:45][N:44]=[N:43][N:42]=2)=[CH:31][CH:30]=1)[C:9]([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 178447297HCID 178447297, compound

Product 1

HCID 178447296HCID 178447296, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

170 mg of (S)-N-(1-benzyloxycarbonyl-5-benzyloxycarbonylamino-pent-1-yl)-N-pentanoyl-N-[2 '-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine are dissolved in 5 ml of methanol. The solution is treated with 170 mg of palladium/carbon (10%) and the mixture is hydrogenated to saturation under normal pressure and at room temperature. The mixture is filtered over Hyflo and the filtrate is evaporated, yielding the pure (S)-N-(5-amino-1-carboxy-pent-1-yl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine in the form of a white foam [MS (FAB): m/z=465, (M+H)+ ].

Workup

  1. customis hydrogenated to saturation under normal pressure and at room temperature
  2. filtrationThe mixture is filtered over Hyflo
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-2209d514efc347abbb02f437f95a3226
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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