Citric Acid → HCID 19010510, compound

HRID 1741747Notes

Reaction equation

HRID 1741747 reaction equation
[OH-].[Na+].[C:3]([CH:7]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH2:18][N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[N:21]=[C:20]2[CH3:28])=[CH:11][C:10]=1[CH2:29][CH2:30][CH3:31])([O:5]C)=[O:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.C(Cl)Cl>[C:3]([CH:7]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH2:18][N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[N:21]=[C:20]2[CH3:28])=[CH:11][C:10]=1[CH2:29][CH2:30][CH3:31])([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 19010505HCID 19010505, compound

Product 1

HCID 19010510HCID 19010510, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 887MethanolSolvent

Procedure

A 5N sodium hydroxide solution (0.4 mL) was added to a stirred mixture of the product of Step D (53.5 mg, 0.104 mmol) in methanol (4 mL). A few drops of methylene chloride were added to allow stirring then the mixture was stirred at room temperature for 2 h. The solution volume was reduced to ~10% in vacuo then 5% citric acid solution was added. The mixture was extracted with ethyl acetate (3 times). The combined organic phase was washed with water, brine, dried (magnesium sulfate) and the solvent removed in vacuo. The residue was chromatographed (8, 10% methanol/methylene chloride) to give the titled compound (28.5 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionThe mixture was extracted with ethyl acetate (3 times)
  3. washThe combined organic phase was washed with water, brine
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe residue was chromatographed (8, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-6667b7b073aa4785b051cca9dfb2400a
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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