Hydrochloric Acid → HCID 10829121, compound

HRID 1736234Notes

Reaction equation

HRID 1736234 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([OH:19])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:29][O:30][CH2:31]Cl.Cl>ClCCl>[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([O:19][CH2:29][O:30][CH3:31])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl Ether3×HCID 81531Diisopropylethylamine3×HCID 10635803HCID 10635803, compound

Product 1

HCID 10829121HCID 10829121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26.6 g of the resulting ethyl 2-(N-ethoxycarbonylamino)-3-fluoro-6-hydroxybenzoate was dissolved in 300 ml of dichloromethane under argon atmosphere, 20.5 ml of diisopropylethylamine and 9.0 ml of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at room temperature for 1.5 hours. Additional 20.5 ml of diisopropylethylamine and 9.0 ml of chloromethyl methyl ether were added and the mixture was stirred for 1.6 hours. Additional 5.1 ml of diisopropylethylamine and 2.2 ml of chloromethyl methyl ether were added and the mixture was stirred for 1 hour. An aqueous dilute solution of hydrochloric acid was added to the reaction solution, the mixture was extracted with dichloromethane, the organic layer was washed with water and an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give ethyl 2-(N-ethoxycarbonylamino)-3-fluoro-6-methoxymethoxybenzoate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.6 hours
  3. stirringthe mixture was stirred for 1 hour
  4. extractionthe mixture was extracted with dichloromethane
  5. washthe organic layer was washed with water
  6. dry with materialan aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5719e7aeace0438a938c7edc41ad73a8
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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