Sulfuric Acid → (S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Participants

Reaction Conditions

Reaction Steps

In a Fischer-Porter tube, a mixture of 22-2 (102 g, 42 mmol) and DME (150 mL) was sequentially treated with H2SO4 (6.4 mL, 0.12 mol), cooled to -78° C., and then condensed isobutylene (75 mL). The cooling bath removed. After 2 h, ice-water (250 mL) was added followed by washing with ether (2×). The aqueous phase was basified with aq 5N NaOH, then saturated with NaCl, followed by extraction with EtOAc (3×). The combined extracts were washed with brine dried (MgSO4), and concentrated to give a white solid. This was dissolved in CHCl3 then treated with 1N HCl/ether (22 mL) then concentrated to give 22-3 as a glossy yellow solid.

Provenance & Evidence