Citric Acid → HCID 9829919, compound

HRID 1090574Notes

Reaction equation

HRID 1090574 reaction equation
C([O:4][C:5]1[CH:45]=[CH:44][C:8]([CH2:9][CH:10]([N:29]([CH3:43])[S:30]([C:33]2[C:34]3[CH:35]=[CH:36][N:37]=[CH:38][C:39]=3[CH:40]=[CH:41][CH:42]=2)(=[O:32])=[O:31])[CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)(O)[O-].[Na+]>CO>[CH2:22]([O:21][C:19]([N:15]1[CH2:16][CH2:17][CH2:18][N:12]([CH2:11][CH:10]([N:29]([CH3:43])[S:30]([C:33]2[C:34]3[CH:35]=[CH:36][N:37]=[CH:38][C:39]=3[CH:40]=[CH:41][CH:42]=2)(=[O:32])=[O:31])[CH2:9][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:45][CH:44]=2)[CH2:13][CH2:14]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 19796310HCID 19796310, compound

Product 1

HCID 9829919HCID 9829919, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

400 mg of the amorphous compound obtained in Example 112 was dissolved in 10 ml of methanol, to the solution was added 2 ml of 10% sodium hydroxide and the mixture was stirred for 10 minutes. The reaction mixture was acidified with citric acid aqueous solution and then alkalized with saturated sodium bicarbonate aqueous solution, and extracted twice with 50 ml of chloroform. The extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform/methanol (100:2) to obtain 339 mg of the title compound in a colorless amorphous form.

Workup

  1. extractionextracted twice with 50 ml of chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customevaporated
  4. customto remove the solvent under a reduced pressure
  5. washeluted with chloroform/methanol (100:2)

Sources & evidence

ORD record
ord-a1bc0b36cc23444db1a4004b2f33da4d
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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