Citric Acid → HCID 19010495, compound

HRID 1741748Notes

Reaction equation

HRID 1741748 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:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=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:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=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 19010494HCID 19010494, compound

Product 1

HCID 19010495HCID 19010495, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 887MethanolSolvent

Procedure

A 5N sodium hydroxide solution (0.2 mL) was added to a stirred mixture of the product of Step A (27 mg, 0.0524 mmol) in methanol (2 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 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 purified by flash-chromatography using silica gel (8, 10% methanol/methylene chloride) to give the titled compound (12.8 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 purified by flash-chromatography

Sources & evidence

ORD record
ord-a6bf3b148a4648daa9683d37ba71dabd
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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