Triethylamine → HCID 70620514, compound

HRID 1679191Notes

Reaction equation

HRID 1679191 reaction equation
[N:1]([CH:4]1[C:29](=[O:30])[N:6]2[C:7]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])=[C:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:9][S:10][C@:5]12[O:31][CH3:32])=[N+]=[N-].CCN(CC)CC>C(Cl)(Cl)Cl>[NH2:1][C@@H:4]1[C:29](=[O:30])[N:6]2[C:7]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])=[C:8]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:9][S:10][C@:5]12[O:31][CH3:32]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 131711054HCID 131711054, compound

Product 1

HCID 70620514HCID 70620514, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of p-nitrobenzyl 7-azido-6-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylate (249 mg., 0.54 mMol) in CHCl3 (5 ml.) is cooled in an ice-bath and treated with Et3N (150 μl, 1.08 mMol). H2S is bubbled through the cold solution for 2-3 mins., followed by N2 for 10 mins. The resulting solution is diluted with cold CH2Cl2 (5 ml.), washed with cold dilute HCl to pH 6, cold H2O (3x) and brine, dried with MgSO4, filtered, and evaporated in vacuo to provide a mixture (245 mg.) of p-nitrobenzyl 7β-amino-6α-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylate and the corresponding 7α-amino-derivative as a yellow foam.

Workup

  1. customH2S is bubbled through the cold solution for 2-3 mins
  2. additionThe resulting solution is diluted with cold CH2Cl2 (5 ml.)
  3. washwashed with cold dilute HCl to pH 6, cold H2O (3x) and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a1e4f58af70d4c8e990482d8891ec128
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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