Water → HCID 10813224, compound

HRID 1736153Notes

Reaction equation

HRID 1736153 reaction equation
[F:1][C:2]1[C:3]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:4]([C:10]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[C:11]([F:14])[C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[CH3:38][O:39][CH2:40]Cl.O>ClCCl>[F:1][C:2]1[C:3]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:4]([C:10]([NH:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[C:11]([F:14])[C:12]=1[O:13][CH2:38][O:39][CH3:40])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 10644727HCID 10644727, compound

Product 1

HCID 10813224HCID 10813224, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.23 g (10.5 mmol) of the above ethyl 3,5-difluoro-4-hydroxy-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate was dissolved in 50 mL of dichloromethane, 2.4 mL (13.7 mmol) of diisopropylethylamine and 0.96 mL (12.6 mmol) of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at the same temperature for 30 minutes. Water was added to the reaction solution and the mixture was extracted once with chloroform. The organic layer was washed once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with n-hexane to give 4.33 g of ethyl 3,5-difluoro-4-methoxymethoxy-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate (yield: 93%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted once with chloroform
  3. washThe organic layer was washed once with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-0a66690d8b7a448895e8c26b3e250848
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…