Water → 4-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester

HRID 1867965Notes

Reaction equation

HRID 1867965 reaction equation
C(OC([NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[NH2:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[O:20])=[O:21])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 579808604-Fluorobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester2×

Product 1

HCID 579808144-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl esterYield 112.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-tert-butoxycarbonylaminobenzo-thiazol-6-yl ester (intermediate 15) (1.7 g, 3.60 mmol), 10 ml of trifluoroacetic acid (130 mmol) in 10 ml of dichloromethane, and 1 ml of water, in a 100 ml round-bottomed flask equipped with a magnetic bar, is stirred for 2 hours at room temperature. The reaction medium is evaporated to dryness and the residue obtained is washed with ethyl ether to give 1.31 g of 4-fluoro-benzenesulfonic acid 2-aminobenzothiazol-6-yl ester in the form of the trifluoroacetic acid salt (white powder) in a yield of 83%.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. customthe residue obtained
  3. washis washed with ethyl ether

Sources & evidence

ORD record
ord-338e7cc0cde5422c9577d7773a06d449
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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