Methanol → HCID 12895880, compound

HRID 894010Notes

Reaction equation

HRID 894010 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:21])[C:17]([O:19]C)=[O:18])=[CH:15][C:9]=3[C:8](=[O:22])[CH2:7][C:6]=2[CH:23]=1.CO.[OH-].[K+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:21])[C:17]([OH:19])=[O:18])=[CH:15][C:9]=3[C:8](=[O:22])[CH2:7][C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 21162411HCID 21162411, compound

Product 1

HCID 12895880HCID 12895880, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 78 mg of methyl 2-(8-amino-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionate and 3 ml of methanol was added with ice cooling 200 mg of potassium hydroxide in 3 ml of water, and the resulting mixture was stirred at room temperature for 6 hours. After filtrating the reaction mixture to remove insoluble substances, the filtrate was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain a yellow solid substance, which was chromatographed over 2 g of silica gel and eluted with chloroform/methanol (50/1), and there were obtained yellow crystals. The thus obtained crystals were recrystallized from chloroform-methanol to obtain 49 mg (yield: 75%) of 2-(8-amino-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as light yellow crystals having a melting point of 189°-191° C.

Workup

  1. filtrationAfter filtrating the reaction mixture
  2. customto remove insoluble substances
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customto obtain a yellow solid substance, which
  8. customwas chromatographed over 2 g of silica gel
  9. washeluted with chloroform/methanol (50/1)
  10. customthere were obtained yellow crystals
  11. customThe thus obtained crystals were recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-01fbb5390e3742aa8d8fd0bb99bbd9cc
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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