Acetic Anhydride → HCID 10254352, compound

HRID 751001Notes

Reaction equation

HRID 751001 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[N:10]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([C:27]([OH:29])=[O:28])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>CCOC(C)=O.O=[Pt]=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[N:10]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:35](=[O:37])[CH3:36])=[C:20]([C:27]([OH:29])=[O:28])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68951461HCID 68951461, compound

Product 1

HCID 10254352HCID 10254352, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxy-N-(3-carboxy-4-nitrophenyl)-N-(3-pyridylmethyl)aniline (200 mg, 0.43 mmol) in 35 mL of EtOAc and 0.1 mL (1.08 mmol) of acetic anhydride was hydrogenated at atmospheric pressure over 20 mg of PtO2 with stirring for 16 hours. The catalyst was removed by filtration and the solution concentrated. The residue was partitioned between 50 mL of DCM and 100 mL of brine. The organic layer was separated, dried (Na2SO4), and concentrated. The residue was chromatographed over SiO2 using MeOH/DCM (1/20) as eluant to give 105 mg (51% yield) of the target compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution concentrated
  3. customThe residue was partitioned between 50 mL of DCM and 100 mL of brine
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed over SiO2

Sources & evidence

ORD record
ord-a3d1a2a9cd3d4bc1ae2af3da4249e67f
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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