HCID 86659597, compound → HCID 70993765, compound

HRID 451322Notes

Reaction equation

HRID 451322 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]([C@@H:21]3[CH2:27][CH2:26][C@@H:25]4[CH2:28][N:22]3[C:23](=[O:37])[N:24]4[O:29]CC3C=CC=CC=3)=[O:20])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]([C@@H:21]3[CH2:27][CH2:26][C@@H:25]4[CH2:28][N:22]3[C:23](=[O:37])[N:24]4[OH:29])=[O:20])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86659597HCID 86659597, compound

Product 1

HCID 70993765HCID 70993765, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 1 (79.6 mg, 0.157 mmol) in methanol (4 mL) and ethyl acetate (2 mL), was added 10% palladium on carbon (18 mg) and the reaction mixture was stirred under an atmosphere of hydrogen (balloon) overnight. LC/MS analysis showed the reaction was not quite complete so an additional 10% palladium on carbon (10 mg) was added and the reaction mixture was stirred under an atmosphere of hydrogen (balloon) for an additional 6 hours. The reaction mixture was filtered through a microfilter and the collected solid was washed well with methanol. The filtrate was concentrated under vacuum and azeotroped with toluene to afford the title compound as a light brown oil which was used directly in the next step without purification

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred under an atmosphere of hydrogen (balloon) for an additional 6 hours
  3. filtrationThe reaction mixture was filtered through a microfilter
  4. washthe collected solid was washed well with methanol
  5. concentrationThe filtrate was concentrated under vacuum
  6. customazeotroped with toluene

Sources & evidence

ORD record
ord-1757832122bb49ec89713dd61577030c
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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