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 2-1b (10.2 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 tube was sealed and the cooling bath was removed. After 24 h, ice/water (250 mL) was added followed by washing with ether (2×). The aqueous phase was basified with aq 6N 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 CH2Cl2 and treated with 1N HCl/ether (22 mL), and then concentrated to give 2-1 as a glassy yellow solid.

Provenance & Evidence