Methanol → HCID 13745627, compound

HRID 986702Notes

Reaction equation

HRID 986702 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18])=[CH:15][C:14]=2[F:28])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].[C:35](OC(=O)C)(=[O:37])[CH3:36].CO>ClCCl.C(N(CC)CC)C.CN(C)C1C=CN=CC=1>[C:35]([O:34][C:5]1[C:6]([CH2:31][CH2:32][CH3:33])=[C:7]([CH:29]=[CH:30][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[O:18])=[CH:15][C:14]=1[F:28])(=[O:37])[CH3:36]

Participants

7

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 13745626HCID 13745626, compound

Product 1

HCID 13745627HCID 13745627, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-dimethylaminopropyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-fluorobenzoate (124 mg) in dichloromethane (1 ml), triethylamine (0.5 ml) and 4-dimethylaminopyridine (a catalytic amount) was added acetic anhydride (0.38 ml). The mixture was stirred well for 1.5 hours at room temperature. To the reaction mixture was added methanol (2 ml), and the solvents removed by evaporation under reduced pressure. The residue was dissolved in chloroform, the solution was washed with a solution of saturated sodium hydrogen carbonate and dried with sodium sulfate, and the solvent was removed by evaporation. The residue was dissolved in ether, and to the solution was added a saturated solution of oxalic acid in ether until a precipitate did not emerge any more. The precipitate was recovered by filtration and washed with ether to give a white solid of 3-dimethylaminopropyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-fluorobenzoate.mono-oxalate (180 mg). M.p. 166°-167° C.

Workup

  1. customthe solvents removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washthe solution was washed with a solution of saturated sodium hydrogen carbonate
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was removed by evaporation
  6. dissolutionThe residue was dissolved in ether
  7. additionto the solution was added a saturated solution of oxalic acid in ether until a precipitate
  8. filtrationThe precipitate was recovered by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-111e7588e2404d309c4a7a44f8c7ac21
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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