Methyl Thioglycolate → (3-Oxo-2-thiophen-2-ylmethyl-2,3-dihydro-1H-isoindol-1-ylsulfanyl)-acetic acid methyl ester

HRID 492228Notes

Reaction equation

HRID 492228 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH2:19][SH:20].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:23][O:22][C:18](=[O:21])[CH2:19][S:20][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 516892Sodium BicarbonateHCID 4616003HCID 4616003, compound

Product 1

HCID 57679339(3-Oxo-2-thiophen-2-ylmethyl-2,3-dihydro-1H-isoindol-1-ylsulfanyl)-acetic acid methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12 (500 mg, 2.04 mmol) in dichloromethane (15 mL) at room temperature was added methyl thioglycolate (204 μL, 2.24 mmol) and the resulting reaction mixture was stirred at room temperature for 18 hours in a sealed tube. The reaction mixture was poured onto saturated sodium bicarbonate and extracted with ethyl acetate (3×30 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 5% EtOAc-Hexanes eluant) provided 650 mg of 13 as a white solid (679 mg theoretical, 96% yield).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e41b0dcc5964f87ac7e00cd85c7f4ae
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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