Water → HCID 86649768, compound

HRID 1880252Notes

Reaction equation

HRID 1880252 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:26][NH:27][C:28](=[O:31])[CH2:29][SH:30].C(N(C(C)C)C(C)C)C.[CH3:41][O:42][CH2:43]Cl.O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:18]=[C:19]([Cl:25])[C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:16])([F:14])[F:15])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:26][NH:27][C:28](=[O:31])[CH2:29][S:30][CH2:41][O:42][CH3:43]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 86649769HCID 86649769, compound

Product 1

HCID 86649768HCID 86649768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.090 g of N-[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl-2-mercaptoacetamide and 0.0446 g of ethyldiisopropylamine in 2 mL of dichloromethane, 0.0278 g of methoxymethyl chloride was added while stirring the solution at 0° C., and the resultant mixture was stirred at room temperature for 1 hour. After the completion of the reaction, 3 mL of water was added to the reaction mixture and the resultant mixture was extracted with chloroform (3 mL×2). The organic phase was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative medium pressure liquid chromatography eluting with ethyl acetate-hexane (a gradient from 1:9 to 1:3) using a medium pressure preparative apparatus (trade name: YFLC-Wprep; manufactured by Yamazen Corporation) to obtain 0.0406 g of the objective substance as a colorless resinoid.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe resultant mixture was extracted with chloroform (3 mL×2)
  3. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by preparative medium pressure liquid chromatography
  6. washeluting with ethyl acetate-hexane (a gradient from 1:9 to 1:3)
  7. customto obtain 0.0406 g of the objective substance as a colorless resinoid

Sources & evidence

ORD record
ord-fb0cd802bde841559ab707a4c407e276
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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