Hydrochloric Acid → HCID 44441080, compound

HRID 2111019Notes

Reaction equation

HRID 2111019 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[CH:15]=[N:16][O:17][C:18]=1[C:19]1[CH:32]=[CH:31][C:22]([CH2:23][S:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=1)=[O:12])[CH3:9].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[CH:15]=[N:16][O:17][C:18]=1[C:19]1[CH:32]=[CH:31][C:22]([CH2:23][S:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:21][CH:20]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68880973HCID 68880973, compound

Product 1

HCID 44441080HCID 44441080, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (1 ml) of methyl 3-(4-[4-[1-(2-chlorophenyl)ethoxy-carbonylamino]-5-isoxazolyl]benzylsulfanyl)propionate (22 mg, 0.046 mmol) in ethanol was added 2N hydrochloric acid (2 ml), and the mixture was stirred at 50° C. for 4 hours. The solvent was evaporated under reduced pressure, and water was added. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (dichloromethane:methanol=9:1) to give the title compound (10 mg, 47%).

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel chromatography (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-6ac75a4d6ef447c38293a9440034ca6f
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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