Citric Acid → HCID 58022566, compound

HRID 2389309Notes

Reaction equation

HRID 2389309 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([NH:29][C:30]([O:32][CH3:33])=[O:31])([CH3:28])[C:23](OCC)=[O:24].[BH4-].[Li+].C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([NH:29][C:30]([O:32][CH3:33])=[O:31])([CH3:28])[CH2:23][OH:24]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 4148881Lithium borohydrideHCID 58022626HCID 58022626, compound

Product 1

HCID 58022566HCID 58022566, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 40 (15.6 g) in THF (249 mL) was added under ice cooling lithium borohydride (3.75 g), and then ethanol (16.6 mL) was added dropwise. The resultant solution was then stirred for 1 hour under ice cooling. To The reaction solution was added 10% aqueous citric acid, extracted with ethyl acetate, washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the target product (12.9 g) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b955acf1d7bd419b8c6ccb84069288a4
Source dataset
uspto-grants-2012_09
Patent number
US08273748B2

Reaction notes

Loading…