HCID 67246279, compound → HCID 67246114, compound

HRID 2425015Notes

Reaction equation

HRID 2425015 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67246279HCID 67246279, compound

Product 1

HCID 67246114HCID 67246114, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound of example 27b (6.0 g; 17.6 mmol) was dissolved in methanol (60 ml) and hydrogenated using 10% Pd—C (50 mg) at 40 psi for 2 h. The reaction mixture was filtered, concentrated and purified using flash chromatography (silica gel, 3% CH3CN in chloroform) to obtain the title compound. Yield, 2.6 g (59%); mp, 183-85° C.; MS (CI): 252 (M++1), 196, 178, 152; analysis: C13H17NO4 requires: C, 62.14; H, 6.82; N, 5.57. found: C, 62.23; H, 6.44; N, 5.57%.

Workup

  1. customfor 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-6a49b6c0032d426db1a908d26e2c2542
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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