Triethylamine → HCID 86735541, compound

Participants

Reaction Steps

A solution of crude p-nitrobenzyl 2-methylthio-5-hydroxy-5-acetoxymethyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (6.31 g., 15.23 mMol) in andydrous CH2Cl2 (75 ml.) is cooled to -78° C. under a N2 atmosphere. Et3N (2.97 ml., 21.3 mMol) is added to the stirring solution followed by dropwise addition of a solution of azidoacetyl chloride (1.85 ml., 21.2 mMol) in CH2Cl2 (20 ml.). The resulting solution is allowed to warm slowly to room temperature. The solution is washed with H2O (3x) and brine, dried with MgSO4, filtered, and concentrated in vacuo to a dark, reddish-brown, viscous oil (7.3 g.). This material is purified by chromatography on silica gel (140 g.). Elution of the column with 10% EtOAc/Oh provides p-nitrobenzyl 7-azido-6-methylthio-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate (4.10 g.) as a dark oil: ir (CHCl3) 2.91, 4.72, 5.58, 5.73, 6.20, 6.55, and 7.39μ; nmr (CDCl3)δ 2.13 (s, 3, COCH3), 2.23 (s, 3, SCH3), 2.83, 3.63 (ABq, 2, J=14Hz, SCH2), 4.17 (s, 1, OH), 4.30, 4.57 (ABq, 2, J=12Hz, CH2OAc), 4.87 (s, 2, H4 and H7), 5.37 (s, 2, CH2Ar), and 7.60, 8.25 (ABq, 4, J=9Hz, ArH); mass spectrum m/e 497 (M+), 469, 454, 422, 414, 368, 354, 341, 311, 299, 278, 261, and 136.

Provenance & Evidence