HCID 70049354, compound → HCID 9808625, compound

HRID 487741Notes

Reaction equation

HRID 487741 reaction equation
C([O:8][C:9]([CH2:11][NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][C@H:24]([C:28]([N:30]2[CH2:47][CH2:46][CH2:45][C@H:31]2[C:32]([NH:34][CH:35]([CH:42]([CH3:44])[CH3:43])[C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[O:33])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])=[CH:17][CH:16]=1)=[O:14])=[O:10])C1C=CC=CC=1.[H][H]>CO.O.[Pd]>[C:9]([CH2:11][NH:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([NH:23][C@H:24]([C:28]([N:30]2[CH2:47][CH2:46][CH2:45][C@H:31]2[C:32]([NH:34][CH:35]([CH:42]([CH3:43])[CH3:44])[C:36](=[O:41])[C:37]([F:39])([F:40])[F:38])=[O:33])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])=[CH:19][CH:20]=1)=[O:14])([OH:10])=[O:8]

Participants

6

Reactant 2

HCID 70049354HCID 70049354, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9808625HCID 9808625, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3(RS)-[[4-[(benzyloxycarbonyl)methylaminocarbonyl]phenylcarbonyl]-L-valyl-L-prolyl]amino-1,1,1-trifluoro-4-methyl-2-oxopentane (70 mg) in a mixture of methanol (10 ml) and water (1 ml) was hydrogenated over 10% palladium on carbon (1.0 g) at 3 atmosphere pressure of hydrogen for 3 hours at room temperature. After the catalyst was removed by filtration, the filtrate was evaporated under reduced pressure to give 3(RS)-[[4-(carboxymethylaminocarbonyl)phenylcarbonyl]-L-valyl-L-prolyl]amino-1,1,1-trifluoro-4-methyl-2-oxopentane (61 mg).

Workup

  1. customAfter the catalyst was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb82c8711b134872890986a6d48ba658
Source dataset
uspto-grants-1994_03
Patent number
US05296591

Reaction notes

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