Citric Acid → HCID 53740490, compound

HRID 1683996Notes

Reaction equation

HRID 1683996 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]3[CH2:21][C@H:20]3[C:22]([O:24]C)=[O:23])=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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]3[CH2:21][C@H:20]3[C:22]([OH:24])=[O:23])=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 53693205HCID 53693205, compound

Product 1

HCID 53740490HCID 53740490, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the ester from Step 2 (145 mg, 0.33 mmol) in 3 mL THF and 3 mL MeOH was added 2N NaOH (1 mL, 2 mmol) and the reaction mixture was stirred at r.t. for 16 h. Excess 0.5N citric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatogrpahy on silicic acid (20% to 40% ethyl acetate in hexane) provided 99 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customPurification by flash chromatogrpahy on silicic acid (20% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0ec3fb2e003d4209b060b49e49585aae
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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