Acetic Anhydride → Methyl 3-(4-{acetyl[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

HRID 508023Notes

Reaction equation

HRID 508023 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([N:16]([CH2:15][C:11]1[CH:10]=[C:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23157312Methyl 3-(4-{[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

Product 1

HCID 23157605Methyl 3-(4-{acetyl[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 3-(4-{[(2′,6′-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate (0.598 g, 1.60 mmol) and acetic anhydride (0.226 mL, 2.40 mmol) in pyridine (3 mL) was stirred at room temperature for 20 hr. The solvent was evaporated by concentration. The obtained residue was diluted with ethyl acetate, washed with 1 M hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30%-60% ethyl acetate/hexane) to give the title compound (0.649 g, yield 98%) as a colorless oil.

Workup

  1. customThe solvent was evaporated by concentration
  2. additionThe obtained residue was diluted with ethyl acetate
  3. washwashed with 1 M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (30%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7e92db98d945410dbb6d6279e490b92d
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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