Citric Acid → HCID 90204397, compound

HRID 1480257Notes

Reaction equation

HRID 1480257 reaction equation
ClC1C=CC(/C=[N:9]/[C:10]([CH3:22])([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C1COCC1.O>C(OCC)(=O)C>[NH2:9][C:10]([CH3:22])([CH2:18][CH:19]1[CH2:21][CH2:20]1)[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 178450943HCID 178450943, compound

Product 1

HCID 90204397HCID 90204397, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 250 mL round-bottomed flask, tert-butyl 2-[(E)-(4-chlorophenyl)methyleneamino]-3-cyclopropyl-2-methyl-propanoate (example 186a, 1.7 g, 5.28 mmol) and citric acid (1.8 g, 9.37 mmol) were combined with THF (30 ml) and water (5 ml) to give a yellow solution. The reaction mixture was stirred at room temperature for 20 h. The reaction mixture was poured into 200 mL ethyl acetate and extracted with an iced 1 M aqueous solution of sodium hydroxide and brine. The aqueous layer was back-extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (452 mg, 43%). MS (ESI, m/z): 200.1 (M+H+).

Workup

  1. customto give a yellow solution
  2. extractionextracted with an iced 1 M aqueous solution of sodium hydroxide and brine
  3. extractionThe aqueous layer was back-extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated down to dryness
  6. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-6d714ef9b591433584a02b6bd2a71736
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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