Hexane → HCID 58619002, compound

Participants

Reaction Steps

To a solution of 27 mg (0.095 mmol) of {4-[(1S)-1-azido-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]cyclohexyl}methanol from isomer II, Example 6, Step J in 1 mL of methylene chloride was added 20 mg (0.1 mmol) of 4-biphenylisocyanate and 0.02 mL of triethylamine. The mixture was stirred for 6 h and directly subjected to preparative TLC (silica gel, 45% ethyl acetate in hexane) to give the carbamate. The carbamate was dissolved in wet THF and to this solution was added 25 mg (excess) of triphenyl phosphine. The reaction mixture was heated at 60° C. for 3 h. Purification by preparative TLC on silica gel (eluent: 10% MeOH in CH2Cl2) gave the title compound. 1H NMR (500 MHz, CD3OD, HCl salt) δ 7.56–7.48 (m, 6H), 7.40 (t, 2H, J=7.5 Hz), 7.28 (t, 1H, J=6.0 Hz), 4.72 (m, 1H), 4.59 (d, 0.45H, J=9.2 Hz), 4.49 (d, 0.55H, J=9.2 Hz), 4.19 (d, 0.45H, J=5.9 Hz), 4.11 (d, 0.55H, J=5.9 Hz), 3.99 (d, 2H, J=6.3 Hz), 3.93 (m, 0.55H), 3.88 (m, 0.45H ), 3.76 (m, 1H), 3.2–3.05 (m, 2H), 1.98–1.80 (m, 5H), 1.71 (m, 1H), 1.27–1.09 (m, 4H).

Provenance & Evidence