Citric Acid → HCID 68625672, compound

HRID 2401305Notes

Reaction equation

HRID 2401305 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[N:17]=3)=[N:12][C:11]([N:24]([CH2:26][CH3:27])[CH3:25])=[N:10][C:9]=2[C:8]([C:28]([O:30]C)=[O:29])=[N:7]1)[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[N:17]=3)=[N:12][C:11]([N:24]([CH2:26][CH3:27])[CH3:25])=[N:10][C:9]=2[C:8]([C:28]([OH:30])=[O:29])=[N:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 68625606HCID 68625606, compound

Product 1

HCID 68625672HCID 68625672, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of step 8 (13.57 g, 32.83 mmol) and a 1M aqueous solution of sodium hydroxide (90 mL) were dissolved in methanol (10 mL) and the reaction mixture stirred at 85 C for 1 hour. The reaction mixture was cooled to room temperature and acidified with 10% aqueous citric acid (90 mL). The aqueous layer was extracted twice with dichloromethane (36 mL and 24 mL). The aqueous layer was further acidified with 10% aqueous citric acid (20 mL) and extracted with dichloromethane (24 mL). The combined dichloromethane extracts were combined and ethanol (13 mL) was added. The solution was distilled at ambient pressure and the distilled dichloromethane replaced with ethanol (52 mL). Water (12 mL) was added and the mixture was cooled to 5 C and stirred for 1 hour. The slurry was filtered and washed with water (24 mL) and dried in vacuo at 55 C to give a yellow solid (8.858 g, 22.2 mmol, 68%)

Workup

  1. extractionThe aqueous layer was extracted twice with dichloromethane (36 mL and 24 mL)
  2. extractionextracted with dichloromethane (24 mL)
  3. additionethanol (13 mL) was added
  4. distillationThe solution was distilled at ambient pressure
  5. additionWater (12 mL) was added
  6. temperaturethe mixture was cooled to 5 C
  7. stirringstirred for 1 hour
  8. filtrationThe slurry was filtered
  9. washwashed with water (24 mL)
  10. customdried in vacuo at 55 C

Sources & evidence

ORD record
ord-92f8b6826e1546eab9add975209a3607
Source dataset
uspto-grants-2014_08
Patent number
US08796287B2

Reaction notes

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