Citric Acid → HCID 71268153, compound

HRID 1519661Notes

Reaction equation

HRID 1519661 reaction equation
[OH-].[K+].C1COCC1.C[O:9][C:10](=[O:28])[C:11]([N:17]([CH3:27])[C:18]([C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)=[O:19])([CH3:16])[C:12]([NH:14][CH3:15])=[O:13].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:10]([C:11]([N:17]([CH3:27])[C:18]([C:20]1[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=1)=[O:19])([CH3:16])[C:12]([NH:14][CH3:15])=[O:13])([OH:28])=[O:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 71268108HCID 71268108, compound2×

Product 1

HCID 71268153HCID 71268153, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.7 mol/L-potassium hydroxide aqueous solution (0.55 mL) was added to a THF (1.0 mL)-MeOH (1.0 mL) solution of 1-{[1-methoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}-4-iodobenzene (Intermediate 10-2, 0.12 g), and the mixture was stirred for 3 hours at room temperature. The reaction mixture was adjusted to pH 5 with a 10% aqueous solution of citric acid, and extracted with a chloroform-methanol mixture. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The desiccant was filtered out, and then the solvent was distilled off under reduced pressure to obtain 1-{[2-carboxy-1-(methylamino)-1-oxopropan-2-yl](methyl)carbamoyl}-4-iodobenzene (Intermediate 11, orange solid) (91 mg, 80%).

Workup

  1. extractionextracted with a chloroform-methanol mixture
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered out
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-31a5a6c135c24ee09d6012ad4699682a
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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