Trifluoroacetic acid → 2-{[4-(Fluorosulfonyl)phenyl]formamido}acetic acid

HRID 382041Notes

Reaction equation

HRID 382041 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([S:16]([F:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:19][S:16]([C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][CH2:7][C:6]([OH:21])=[O:5])=[O:20])=[CH:15][CH:14]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53723910(4-Fluorosulfonyl-benzoylamino)-acetic acid tert-butyl ester

Product 1

HCID 183638592-{[4-(Fluorosulfonyl)phenyl]formamido}acetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the crude (4-fluorosulfonyl-benzoylamino)-acetic acid tert-butyl ester (541 mg, 1.70 mmol) (from step A above) in 2 mL of methylene chloride was treated with 2 mL of trifluoroacetic acid. The reaction mixture was stirred at room temperature for 72 h. The reaction mixture was concentrated in vacuo to provide crude (4-fluorosulfonyl-benzoylamino)-acetic acid (407.9 mg, 92%) as a solid that was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-9da355ff443244fa9560eb80b246a695
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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