Reaction #2257290

Reaction equation

methyl 3-(chlorosulfonyl)benzoate

1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester

1-Aminomethyl-cyclobutanecarboxylic acid tert-butyl ester

→

title compound

3-[(1-tert-Butoxycarbonyl-cyclobutylmethyl)-sulfamoyl]-benzoic acid methyl ester

Solvents

DCM

Conditions

Workup

1. 1
   Otherpartitioned between DCM and water
2. 2
   ExtractionThe aqueous portion was extracted with DCM
3. 3
   Washthe combined organic extracts were washed with 0.1N HCl, brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane

Procedure

A solution of 1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester (step 2) (1.47 g, 7.38 mmol) in DCM (40 ml) was treated with TEA (2.57 ml, 18.44 mmol) followed by methyl 3-(chlorosulfonyl)benzoate (1.91 g, 8.11 mmol) and DMAP (0.09 g, 0.74 mmol). The mixture was stirred at RT for 2 h and then partitioned between DCM and water. The aqueous portion was extracted with DCM and the combined organic extracts were washed with 0.1N HCl, brine, dried over MgSO4 and concentrated in vacuo. Purification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the title compound as a colourless oil; 1H NMR (400 MHz, CDCl3) δ 8.56 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.64 (1H, t), 5.21 (1H, br t), 3.98 (3H, s), 3.20 (2H, d), 2.37 (2H, m), 1.96 (4H, m), 1.46 (9H, s).

Source