Acetyl chloride → 1-acetylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19559Notes

Reaction equation

HRID 19559 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH2:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[C:24](Cl)(=[O:26])[CH3:25].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:23][C:24](=[O:26])[CH3:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 116739651-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 116674761-acetylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (60 mg, 0.19 mmol) prepared in Example 20 was dissolved in dichloromethane (10 mL), and acetyl chloride (76.15 mg, 70.0 μl, 0.97 mmol) and triethylamine (130.00 mg, 0.18 mL, 128 mmol) were added thereto in order at 0° C. The mixture was stirred for 1 hr at RT, washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 48 mg of the titled compound (yield: 71%).

Workup

  1. customat 0° C
  2. washwashed with saturated saline
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-57f58d076584492c981c33d3ab69813d
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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