HCID 18390924, compound → HCID 86754373, compound

HRID 1584411Notes

Reaction equation

HRID 1584411 reaction equation
[C:1]([O:5][NH:6][C:7](=[O:44])[C@@H:8]([NH:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:42])[CH3:41])[NH:29]C(OCC1C=CC=CC=1)=O)[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])([CH3:4])([CH3:3])[CH3:2]>CO.C(O)C.[Pd]>[C:1]([O:5][NH:6][C:7](=[O:44])[C@@H:8]([NH:26][C:27](=[O:43])[C@H:28]([CH:40]([CH3:41])[CH3:42])[NH2:29])[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:15][CH:14]=1)(=[O:11])=[O:12])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 1

HCID 18390924HCID 18390924, compound

Product 1

HCID 86754373HCID 86754373, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of (R)-N-tert-butoxy-2-(CBZ-valinamido)-3-(4-phenoxyphenylsulfonyl)-propionamide (prepared above) in a mixture of methanol (300 ml) and ethanol (100 ml) was stirred under hydrogen at 1 atmosphere with palladium on carbon catalyst (10% Pd, 4 g) for 3 hours. The mixture was filtered, and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with 0-3% methanol in methylene chloride, to give (R)-N-tert-butoxy-2-valinamido-3-(4-phenoxyphenylsulfonyl)-propionamide (1.6 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with 0-3% methanol in methylene chloride

Sources & evidence

ORD record
ord-aef83d333af14d9b96a9f9985d530c37
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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