Hydrochloric Acid → HCID 59013465, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl chloroformate (114 mg, 1.20 mmol) in CH2Cl2 (0.5 mL) was added dropwise to a solution of (1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-6′-(hydroxymethyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3′,4′,5′-triol (compound AV) (418 mg, 1.00 mmol) in 2,4,6-collidine (5 mL) at −40° C. The whole was stirred at −40° C. for 1 h and at room temperature for 1.5 h. The reaction mixture was poured into ice-cooled 10% HCl and extracted with AcOEt. The organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica gel to give the acylated product BH (420 mg, 87%). 1H NMR (CD3OD, 300 MHz) δ 7.25 (s, 1H), 7.23 (s, 1H), 7.09 (m, 4H), 4.05 (s, 2H), 3.80 (m, 1H), 3.65 (s, 3H), 3.62-3.34 (m, 5H), 2.91 (dd, J=6.6, 7.8 Hz, 2H), 2.60 (q, J=7.8 Hz, 2H), 2.55 (dt, J=7.5, 13.2 Hz, 1H), 2.10 (dt, J=7.5, 13.2 Hz, 1H), 1.20 (t, J=7.8 Hz, 3H); MS ESI m/e 477 (M+1).

Provenance & Evidence