Water → HCID 22671960, compound

HRID 1279616Notes

Reaction equation

HRID 1279616 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:3]=1[O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:43]1([S:48](Cl)(=O)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44]1.O>C(Cl)Cl.N1C=CC=CC=1>[CH:43]1([S:48]([NH:1][C:2]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][C:3]=2[O:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=2)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 3717197Cyclopentanesulfonyl chlorideHCID 12017679HCID 12017679, compound

Product 1

HCID 22671960HCID 22671960, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(2-amino-5-trifluoromethylphenoxymethyl)benzoate (300 mg) in methylene chloride (3.0 ml), pyridine (187 μml) and triphenylphosphine (315 mg) were added in a stream of argon. At 0° C., cyclopentylsulfonylchloride (202 mg) was added dropwise thereto. The mixture was stirred for 6 hours at room temperature. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate, washed, dried over and concentrated with the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=2:1→1:1) to give the title compound (309 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed
  3. customdried over and
  4. concentrationconcentrated with the reduced pressure
  5. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=2:1→1:1)

Sources & evidence

ORD record
ord-0f1abf5f9f2d41f0a687b611e2068c44
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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