Acetic Acid → HCID 18688666, compound

HRID 1873236Notes

Reaction equation

HRID 1873236 reaction equation
COC([CH:5]1[C:11](=O)[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8][C:7]2[CH:17]=[CH:18][C:19]([CH:21]([CH3:26])[C:22]([O:24]C)=[O:23])=[CH:20][C:6]1=2)=O.C(O)(=O)C.Cl.[OH2:32]>>[O:32]=[C:5]1[CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8][C:7]2[CH:17]=[CH:18][C:19]([CH:21]([CH3:26])[C:22]([OH:24])=[O:23])=[CH:20][C:6]1=2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 18688662HCID 18688662, compound

Product 1

HCID 18688666HCID 18688666, compound

Procedure

Methyl 2-(10,11-dihydro-1i-methoxycarbonyl-10-oxodibenzo[b,f]thiepin-2-yl)propionate (prepared in Example 22, 18 mg, 0.040 mmol.), acetic acid (0.3 mL) and 6N hydrochloric acid (0.3 mL) were mixed, and the mixture was heated for 2 hours under reflux. To the reaction mixture was added water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate portion was washed successively with water and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried ethyl acetate portion was placed under reduced pressure to distill the solvent off. The residue was dissolved in toluene and concentrated under reduced pressure to give 14 mg of the desired compound as a white crystalline product.

Workup

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureunder reflux
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe ethyl acetate portion was washed successively with water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. distillationto distill the solvent off
  7. dissolutionThe residue was dissolved in toluene
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21f1231ee96e4a5f9cdcf2a5c59704b7
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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