Tributylphosphine → HCID 54246547, compound

Participants

Reaction Steps

1,1′-(Azodicarbonyl)dipiperidine (680 mg, 2.7 mM) was added portionwise to a stirred solution of 3-t-butyloxycarbonylamino-1,2,5-thiadiazole (543 mg, 2.7 mM, see WO 93-13091), 3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (720 mg, 1.8 mM; prepared by analogy with 3-fluoro compound—see WO 97-30995) and tributylphosphine (540 mg, 2.7 mM) in dry tetrahydrofuran (25 ml) at 0° under nitrogen. The mixture was stirred at 0° for 30 minutes and then at ambient temperature for 3 hours. The mixture was filtered and the filtrate evaporated. The residue was purified, firstly on a silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 30% ethyl acetate in isohexane and then on an Isolute SCX ion exchange column, washing with a gradient increasing, in polarity from 0 to 10% methanol in dichloromethane and then eluting with dichloromethane/methanol/0.88SG ammonia 87:10:3 to give the title product as a solid (669 mg, 64% ). NMR (DMSO-d6) δ: 1.49 (s, 9H); 2.30 (brs, 2H); 2.61 (t, 2H); 3.04 (m, 2H); 3.58 (s, 2H); 3.88 (dd, 1H); 4.13 (dd, 1H); 4.20 (dd, 1 H); 4.35 (dd, 1H); 5.02 (m, 1H); 5.79 (brs, 1H); 7.20-7.33 (m, 7H); 8.96 (s, 1H). MS (ESP): 584 (MH+) for C29H31F2N5O4S

Provenance & Evidence