Trifluoroacetic acid → 4-Fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl ester

HRID 1867955Notes

Reaction equation

HRID 1867955 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:36])[NH:15][C:16]2[S:17][C:18]3[CH:24]=[C:23]([O:25][S:26]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:15][C:16]2[S:17][C:18]3[CH:24]=[C:23]([O:25][S:26]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)(=[O:28])=[O:27])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:36])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579808264-[6-(4-Fluorobenzenesulfonyloxy)benzothiazol-2-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 579808454-Fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl esterYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[6-(4-fluorobenzenesulfonyloxy)benzothiazol-2-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (intermediate 3) (100 mg, 0.187 mmol) and of TFA (0.5 ml) in dichloromethane (4.5 ml) is stirred at room temperature for 1 hour. The reaction medium is evaporated to dryness. The residue is taken up in a minimum amount of water, neutralized by addition of aqueous 10% Na2CO3 solution and extracted with ethyl acetate to give 55 mg of 4-fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]benzo-thiazol-6-yl ester (white solid).

Workup

  1. customThe reaction medium is evaporated to dryness
  2. additionneutralized by addition of aqueous 10% Na2CO3 solution
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-63821ab16bff4138b576198f0458a0a0
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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