Water → HCID 131727976, compound

HRID 2243484Notes

Reaction equation

HRID 2243484 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18]([C:20]1[S:24][C:23]2[CH:25]=[C:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:27]=[CH:28][C:22]=2[C:21]=1O)=[O:19].O.CCOC(C)=O>C(Cl)Cl.CCN(CC)CC>[CH3:16][O:17][C:18]([C:20]1[S:24][C:23]2[CH:25]=[C:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:27]=[CH:28][C:22]=2[C:21]=1[O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 57581739HCID 57581739, compound

Product 1

HCID 131727976HCID 131727976, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Trifluoromethanesulfonic anhydride (4.6 ml 27 mmol, 1.5 equiv) was dropwise added to a 0° C. solution of 3-hydroxy-benzo[b]thiophene-2,6-dicarboxylic acid 6-tert-butyl ester 2-methyl ester (5.56 g, 18 mmol) in DCM (50 ml) and Et3N (50 ml). The reaction mixture was warmed to RT and stirred for 30 min. After adding water and EtOAc the crude reaction mixture was washed with sat. NaHCO3 then dried over MgSO4. Filtration, evaporation, and purification by column chromatography yielded 4.56 g (57%) of 3-trifluoromethanesulfonyloxy-benzo[b]thiophene-2,6-dicarboxylic acid 6-tert-butyl ester 2-methy ester. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.64 (s, 9H) 4.01 (s, 3H) 7.87 (d, J=8.59 Hz, 1H) 8.12 (dd, J=8.59, 1.52 Hz, 1H) 8.50 (s, 1H). HRMS (ESI+, m/z) calcd for [M+NA]1+, 463.01035, found 463.01013.

Workup

  1. customreaction mixture
  2. washwas washed with sat. NaHCO3
  3. dry with materialthen dried over MgSO4
  4. filtrationFiltration, evaporation, and purification by column chromatography

Sources & evidence

ORD record
ord-41ad2756700a4f598fe245c8762f8fa8
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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