Citric Acid → HCID 58124870, compound

HRID 1971758Notes

Reaction equation

HRID 1971758 reaction equation
[C:1]([N:5]1[CH2:34][CH2:33][CH2:32][CH2:31][C:8]2[C:9]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]([O:22]C)=[O:21])[C:16]([O:24][CH3:25])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:35])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[C:1]([N:5]1[CH2:34][CH2:33][CH2:32][CH2:31][C:8]2[C:9]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]([OH:22])=[O:21])[C:16]([O:24][CH3:25])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:35])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 58124850HCID 58124850, compound

Product 1

HCID 58124870HCID 58124870, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 480 mg 26a in 10 mL methanol was added a solution of 164 mg potassium hydroxide in 10 mL water. The mixture was stirred at 80° C. for 5 h and then at 50° C. for 16 h. The reaction mixture was poured into a 2M solution of citric acid in water and was extracted with 2×50 mL dichloromethane. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to give 460 mg of compound 26b.

Workup

  1. waitat 50° C. for 16 h
  2. extractionwas extracted with 2×50 mL dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-80044b5880684567b3da4ae69d6e9278
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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