Citric Acid → HCID 59075932, compound

HRID 1356564Notes

Reaction equation

HRID 1356564 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[CH:11]=[C:10](N3CCCC3)[CH:9]2[C:26]([O:28][CH3:29])=[O:27])=[CH:4][CH:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:33]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[CH2:11][C:10]([OH:33])=[C:9]2[C:26]([O:28][CH3:29])=[O:27])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 311Citric AcidHCID 18509170HCID 18509170, compound

Product 1

HCID 59075932HCID 59075932, compound

Conditions

Temperature
60 °C

Procedure

A suspension of 13.0 g (32.7 mmol) of the compound of Example XII in 1100 ml of a sat. solution of citric acid is stirred at 60° C. for 16 h. The mixture is allowed to cool and extracted with ethyl acetate (3×600 ml). The combined organic phases are washed with sat. NaCl solution and dried over Na2SO4, giving a yellow residue which is purified by flash filtration over 450 g silica gel 60 using EtOAc/cyclohexane 1:20 to 20:1.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×600 ml)
  3. washThe combined organic phases are washed with sat. NaCl solution
  4. dry with materialdried over Na2SO4
  5. customgiving a yellow residue which
  6. filtrationis purified by flash filtration over 450 g silica gel 60 using EtOAc/cyclohexane 1:20 to 20:1

Sources & evidence

ORD record
ord-1827f819d4db402c964a5cfec7f742f5
Source dataset
uspto-grants-2003_07
Patent number
US06586613B1

Reaction notes

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