HCID 53919629, compound → HCID 54310096, compound

HRID 279717Notes

Reaction equation

HRID 279717 reaction equation
C([O:8][NH:9][C:10](=[O:37])[C@H:11]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:12][C:13](=[O:29])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])C1C=CC=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[OH:8][NH:9][C:10](=[O:37])[C@H:11]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:12][C:13](=[O:29])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20]

Participants

4

Reactant 1

HCID 53919629HCID 53919629, compound

Product 1

HCID 54310096HCID 54310096, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

N-(Toluene-4-sulfonyl)-L-prolyl-L-phenylalanine N-benzyloxyamide (see Example 43 (159)) was dissolved in MeOH (10 mL) and 5% Pd/BaSO4 (52 mg) was added. The mixture was hydrogenated at 50 psi H2 for 9 h. The mixture was filtered through a pad of diatomaceous earth and evaporated in vacuo to give a residue which was purified by silica gel chromatography (92:8 CH2Cl2/MeOH) to give the title compound as an oil.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. customevaporated in vacuo
  3. customto give a residue which
  4. customwas purified by silica gel chromatography (92:8 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-bd24aa220ba54693b604348b3a25d0d4
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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