Sodium Hydroxide → HCID 9823986, compound

HRID 1684001Notes

Reaction equation

HRID 1684001 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C@@H:19]([CH3:25])[CH2:20][C:21]([O:23]C)=[O:22])=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C@@H:19]([CH3:25])[CH2:20][C:21]([OH:23])=[O:22])=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53651857HCID 53651857, compound

Product 1

HCID 9823986HCID 9823986, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester from Step 4 (75 mg) in THF (1.5 mL) and methanol (1.5 mL) there was added 1N aq. NaOH (1 mL) and the mixture was refluxed for 1 h. The mixture was concentrated until solids appeared, diluted with water and acidified with 1N aq. HCl (2 mL). The mixture was extracted twice with ether, the extracts washed twice with water, dried and evaporated to a solid residue which was triturated with hexane and filtered, affording the title compound as a cream colored solid (61 mg). [α]D =-4.4° (c=1, acetone)

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. concentrationThe mixture was concentrated until solids
  3. additiondiluted with water
  4. extractionThe mixture was extracted twice with ether
  5. washthe extracts washed twice with water
  6. customdried
  7. customevaporated to a solid residue which
  8. customwas triturated with hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-89c08547cff24bbda7d8e8191615219d
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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