Hydrochloric Acid → HCID 23003230, compound

HRID 396558Notes

Reaction equation

HRID 396558 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[O:21][N:20]=[C:19]([C:22]([O:24]CC)=[O:23])[CH:18]=1)=[O:16].Cl>C(O)(=O)C>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:15]([C:17]1[O:21][N:20]=[C:19]([C:22]([OH:24])=[O:23])[CH:18]=1)=[O:16])=[C:5]2[CH2:4][C:3]([OH:27])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23003237HCID 23003237, compound

Product 1

HCID 23003230HCID 23003230, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl[5-chloro-2-[3-(ethoxycarbonyl)isoxazole-5-carbonyl]-1H-indol-3-yl]acetate (Example 259, 314 mg, 0.80 mmol) in acetic acid (20 ml) was added 2N aqueous HCl (6.0 ml) and the mixture was heated at 110° C. for 5 h. The mixture was then cooled to room temperature and concentrated. The residual yellow solids were washed with ethyl acetate and recrystallized from ethyl acetate/hexane to afford 120 mg (43%) of the title compound as pale yellow solids.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. washThe residual yellow solids were washed with ethyl acetate
  4. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a93259a5d51940f2803517bea0d2eee8
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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