Hydrochloric Acid → HCID 10806525, compound

HRID 1736243Notes

Reaction equation

HRID 1736243 reaction equation
[F:1][C:2]1[C:3]([OH:20])=[C:4]([C:10]([NH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[CH3:30][O:31][CH2:32]Cl.Cl>ClCCl>[F:1][C:2]1[C:3]([O:20][CH2:30][O:31][CH3:32])=[C:4]([C:10]([NH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([F:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 10803339HCID 10803339, compound

Product 1

HCID 10806525HCID 10806525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.72 g of the above ethyl 3,5-difluoro-6-(N-ethoxycarbonylamino)-2-hydroxybenzoate was dissolved in 70 mL of dichloromethane under argon atmosphere, 4.13 mL of diisopropylethylamine and 1.80 mL of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at 0° C. for 20 minutes. Dilute hydrochloric acid was added to the reaction solution and the mixture was extracted with ether. 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 3,5-difluoro-6-(N-ethoxycarbonylamino)-2-methoxymethoxybenzoate.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ac42836e874c48949ea9c62d2d2b1d31
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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