HCID 76578029, compound → HCID 76578026, compound

HRID 910409Notes

Reaction equation

HRID 910409 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([N:8]1[C:12](=[O:13])[CH:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:10][C:9]1=[O:22])[CH:5]([CH3:7])[CH3:6]>Cl>[O:22]=[C:9]1[NH:10][CH:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:13])[N:8]1[CH:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:23])=[O:2]

Participants

3

Reactant 1

HCID 76578029HCID 76578029, compound

Product 1

HCID 76578026HCID 76578026, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the compound obtained in step d above (482 mg, 1.52 mmol) and 6 N HCl (20 mL) was stirred at 70° C. for 3 h. The reaction mixture was cooled to room temperature and extracted with CH2Cl2. The combined organic phases were washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a colorless oil (210 mg, 46% yield) with a recover of starting material (200 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9f639a23e1c458b819fd1e6f1aad593
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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