Citric Acid → HCID 86718260, compound

HRID 922740Notes

Reaction equation

HRID 922740 reaction equation
C[O:2][C:3]([C:5]12[O:11][CH2:10][C:9]1([CH3:12])[CH2:8][CH2:7][CH:6]2[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:6]2[C:5]3([CH2:3][OH:2])[C:9]([CH3:12])([CH2:10][O:11]3)[CH2:8][CH2:7]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86718261HCID 86718261, compound

Product 1

HCID 86718260HCID 86718260, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In 20 ml of ethanol, 970.6 mg of Compound 7a-1 synthesized in Production Example 18 was dissolved. Thereafter, the solution thus obtained was cooled to 0° C. To the solution thus cooled, 249 mg of sodium borohydride and 365 mg of calcium chloride (powder) were added. The resulting mixture was stirred at 0° C. for 2 hours. After the reaction, the reaction was stopped with an aqueous solution of 1 mol/l citric acid. Then, extraction with ethyl acetate was carried out. The organic layer thus extracted was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 845.3 mg of Compound 8a-1.

Workup

  1. dissolutionwas dissolved
  2. customThereafter, the solution thus obtained
  3. temperatureTo the solution thus cooled
  4. customAfter the reaction
  5. extractionThen, extraction with ethyl acetate
  6. extractionThe organic layer thus extracted
  7. washwas washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled away
  10. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa729ba4e3c44e5e96fb764e6c44c662
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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