Trifluoroacetic acid → 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

HRID 1872232Notes

Reaction equation

HRID 1872232 reaction equation
C([O:5][C:6]([CH:8]1[CH:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:17]([O:16][CH2:15][CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH:8]1[C:6]([OH:7])=[O:5])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 540629683-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Product 1

HCID 186896413-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (266 mg, 0.6 mmoL) in 1.5 mL dichloromethane at 0° C. was added 1.5 mL of trifluoroacetic acid. The reaction was gradually allowed to warm to ambient temperature, and the solvent was removed under reduced pressure after 1.4 hours. The residue was azeotroped twice with toluene and purified by column chromatography (silica: 30% ethyl acetate in hexanes with 1% acetic acid to 4% methanol in dichloromethane with 1% acetic acid) to yield 3-Acetoxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid quantitatively; MS: (M+H)+ =386, (M+NH4)+ =403.

Workup

  1. customthe solvent was removed under reduced pressure after 1.4 hours
  2. customThe residue was azeotroped twice with toluene
  3. custompurified by column chromatography (silica: 30% ethyl acetate in hexanes with 1% acetic acid to 4% methanol in dichloromethane with 1% acetic acid)

Sources & evidence

ORD record
ord-b9d1066ac9cf42cd904edbd57142a604
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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