Trifluoroacetic acid → 5-(2-Carboxy-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

HRID 583354Notes

Reaction equation

HRID 583354 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH:7]=[C:6]([CH3:19])[C:5]=1[N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21].FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[C:6]([CH3:19])[C:5]=1[N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 700548965-(2-tert-Butoxycarbonyl-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

Product 1

HCID 700551955-(2-Carboxy-vinyl)-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl esterYield 95.4%

Procedure

To a solution of 237.8 mg (0.5 mmol) of the product of Example 203 in 2 ml dichlocomethane, was added lml of trifluoroacetic acid and the reaction was stirre at room temperature for 2 h. The resulting mixture was concentrated in vacuo to provide 200 mg (95%) of the desired product as a white solid after trituration with hexane/ether (2:1). Electrospray Mass Spec 418(M-H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-53a75ed56200493a9bddc196a05214fe
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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