Methyl 2-hydroxy-3-propionylbenzoate → Methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate

HRID 1452314Notes

Reaction equation

HRID 1452314 reaction equation
[OH:1][C:2]1[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:16]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C1C=CN=CC=1.ClCCl>[CH:16]1([C:23]([O:1][C:2]2[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 10899812Methyl 2-hydroxy-3-propionylbenzoateHCID 12556870Cycloheptanecarbonyl chloride

Product 1

HCID 19972577Methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture, of 7.3 g of methyl 2-hydroxy-3-propionylbenzoate, 4.7 g of 4-dimethylaminopyridine and 50 ml of dichloromethane was stirred at room temperature. Cycloheptanecarbonyl chloride, 56 g, in 10 ml of dichloromethane, (prepared as described in P. W. Collins et al., J. Med. Chem. 32, 1001-1006 (1989)) was added to the solution using dropwise addition. The mixture was stirred at room temperature for 5 hours and allowed to stand overnight. The reaction mixture was washed, in succession, with 3% hydrochloric acid, saturated aqueous sodium bicarbonate solution and water. This was followed by drying over anhydrous sodium sulfate and evaporation to dryness to provide 9.8 g of crude methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate. This product was utilized without further purification.

Workup

  1. additionwas added to the solution
  2. additionaddition
  3. waitto stand overnight
  4. washThe reaction mixture was washed, in succession, with 3% hydrochloric acid, saturated aqueous sodium bicarbonate solution and water
  5. dry with materialby drying over anhydrous sodium sulfate and evaporation to dryness

Sources & evidence

ORD record
ord-902be35490e84e1abd21a94220bdf706
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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