4-Toluenesulfonyl chloride → HCID 59201644, compound

Participants

Reaction Steps

The tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-hydroxypropan-2-ylcarbamate (1.70 g, 5.92 mmol) and tosyl chloride (4.5 g, 23.7 mmol, 4.0 equiv) were dissolved in pyridine (30 mL) and the mixture stirred at room temperature for 17 hr. The pyridine was removed in vacuo and the residue partitioned between EtOAc and 1.0 M HCl. The layers were separated and the organic layer washed with brine, dried over Na2SO4, filtered and evaporated. The (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was purified by flash chromatography on silica eluting with 0-29% EtOAc in hexanes. The fractions were evaporated and used directly in the next step. MS ESI +ve m/z 464 (M+Na).

Provenance & Evidence