Water → HCID 68546570, compound

HRID 2243485Notes

Reaction equation

HRID 2243485 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[CH3:7][O:8][C:9]([C:11]1[S:15][C:14]2[CH:16]=[C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:18]=[CH:19][C:13]=2[C:12]=1OS(C(F)(F)F)(=O)=O)=[O:10].O>C(Cl)Cl.CCN(CC)CC>[CH3:7][O:8][C:9]([C:11]1[S:15][C:14]2[CH:16]=[C:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH:18]=[CH:19][C:13]=2[C:12]=1[S:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 16907Methyl ThioglycolateHCID 131727976HCID 131727976, compound

Product 1

HCID 68546570HCID 68546570, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methyl thioglycolate (1.1 ml, 12 mmol) was added to a solution of 3-trifluoromethanesulfonyloxy-benzo[b]thiophene-2,6-dicarboxylic acid 6-tert-butyl ester 2-methy ester in DCM (30 ml) and Et3N (15 ml) and stirred for 24 hr at RT then 24 hr at 40° C. When the starting material was absent in LC trace, water was added. Extraction with EtOAc and evaporation left an orange liquid. Purification by column chromatography yielded 2.7 g (70%) of 3-methoxycarbonylmethylsulfanyl-benzo[b]thiophene-2,6-dicarboxylic acid 6-tert-butyl ester 2-methyl ester.

Workup

  1. custom24 hr
  2. customat 40° C
  3. additionwas added
  4. extractionExtraction
  5. customwith EtOAc and evaporation
  6. waitleft an orange liquid
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-d753cd50e47247a38576740bcd3efc1d
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…