Methanol → HCID 67814402, compound

HRID 2401388Notes

Reaction equation

HRID 2401388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[C@H:10]([CH2:23][C:24]([OH:26])=[O:25])[N:9]=2)=[CH:4][CH:3]=1.[C:27](Cl)(=O)C(Cl)=O.CO>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:19]([CH3:22])=[N:20][O:21][C:11]=3[C@H:10]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 67815062HCID 67815062, compound

Product 1

HCID 67814402HCID 67814402, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetic acid (100 mg, 0.27 mmol) and N,N-dimethylformamide (1 drop) in dichloromethane (10 mL) was added oxalyl chloride (56 mg, 0.40 mmol) dropwise at 0° C. The mixture was stirred for 0.5 hour at room temperature. The solution was cooled to 0° C. and methanol (100 mL) was added. The mixture was stirred for 0.5 hour at room temperature. The mixture was concentrated in vacuo, and the residue was diluted with water (5 mL), and extracted with ethyl acetate (10 mL×3). The combined organic layers were dried by sodium sulfate, concentrated in vacuo and the residue was purified by column chromatography (silica-gel, petroleum:ethyl acetate=2:1) to give methyl 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (80 mg, 77%) as a light yellow solid. LC/MS m/z 380 [M+H]+.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe mixture was stirred for 0.5 hour at room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was diluted with water (5 mL)
  5. extractionextracted with ethyl acetate (10 mL×3)
  6. dry with materialThe combined organic layers were dried by sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by column chromatography (silica-gel, petroleum:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3bfc4efa67c54baaa0d5f9d35ed642ec
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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