Water → HCID 22671960, compound

HRID 1006551Notes

Reaction equation

HRID 1006551 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 μl) 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-6b94539d9b2947879b0476e4997f9239
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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