Triethylamine → HCID 131711053, compound

HRID 1679188Notes

Reaction equation

HRID 1679188 reaction equation
[N:1]([CH:4]1[C:34](=[O:35])[N:6]2[CH:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:8]([CH2:16][O:17][C:18](=[O:20])[CH3:19])(OS(C)(=O)=O)[CH2:9][S:10][C@:5]12[S:36][CH3:37])=[N+:2]=[N-:3].CCN(CC)CC>C(Cl)Cl>[N:1]([CH:4]1[C:34](=[O:35])[N:6]2[C:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])=[C:8]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:9][S:10][C@:5]12[S:36][CH3:37])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86735542HCID 86735542, compound

Product 1

HCID 131711053HCID 131711053, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethyl-3-methylsulfonyloxy-cepham-4-carboxylate (211 mg., 0.366 mMol) and Et3N (102 μ1., 0.732 mMol) in anhydrous CH2Cl2 (2 ml.) is stirred at room temperature for 35 mins. The solution is washed with H2O (2x), 10% HCl, H2O, and brine, dried with MgSO4, filtered, and evaporated in vacuo to yield p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethylceph-3-em-4-carboxylate (169 mg.) as an oil: ir (neat) 4.72, 5.59, 5.75, 6.55, and 7.40μ; nmr (CDCl3) 2.08 (s, 3, COCH3, 2.18 (s, 3, SCH3), 3.43, 3.95 (ABq, 2, J=19Hz, SCH2), 4.77 (s, 1, H7) 4.83, 5.17 (ABq, 2, J=14Hz, CH2OAc), 5.38 (s, 2, CH2Ar), and 7.57, 8.23 (ABq, 4, J=8.5Hz, ArH); mass spectrum m/e 479 (M+), 451, 436, 404, 392, 271, 260, 216, 200, and 136.

Workup

  1. washThe solution is washed with H2O (2x), 10% HCl, H2O, and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-210c65a9033e41488ebacedbf2a9a169
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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