Sodium Hydroxide → HCID 19041666, compound

HRID 1683979Notes

Reaction equation

HRID 1683979 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[C:10]=2[CH3:28])[CH2:8][CH2:7]1.[OH-].[Na+]>CO.CCOCC.CCCCCC>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:11]2[C:12]3[C:17](=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9]([C:6]3([CH2:5][CH2:4][C:3]([OH:29])=[O:2])[CH2:8][CH2:7]3)=[C:10]2[CH3:28])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19041699HCID 19041699, compound

Product 1

HCID 19041666HCID 19041666, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To a solution of ester from Step 11 (150 mg, 0.33 mmol) in 5 mL MeOH was added 2N NaOH (0.5 mL, 1 mmol). The reaction mixture was heated to reflux for 3 h then cooled and partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was filtered through a plug of silicic acid and the solid obtained was swished in (1: 1 ) Et2O-hexane. Collection of the solid provided 110 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. temperaturethen cooled
  4. custompartitioned between 1N HCl and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. filtrationThe residue was filtered through a plug of silicic acid
  9. customthe solid obtained
  10. customCollection of the solid

Sources & evidence

ORD record
ord-636a7f65e36a451e9d47a7a05f99a849
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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