Triethylamine → p-Nitrobenzyl 7alpha-azido-3-methanesulfonyloxy-3-acetoxymethyl-cepham-4-carboxylate

HRID 866482Notes

Reaction equation

HRID 866482 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]([C@H:9]1[C:35](=[O:36])[N:11]2[CH:12]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[C:13]([OH:21])([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:14][S:15][C@H:10]12)=[N+:7]=[N-:8].CCN(CC)CC>C(Cl)Cl>[N:6]([C@H:9]1[C:35](=[O:36])[N:11]2[CH:12]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[C:13]([O:21][S:2]([CH3:1])(=[O:4])=[O:3])([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:14][S:15][C@H:10]12)=[N+:7]=[N-:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86735841p-Nitrobenzyl 7alpha-azido-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate

Product 1

HCID 86735840p-Nitrobenzyl 7alpha-azido-3-methanesulfonyloxy-3-acetoxymethyl-cepham-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (0.145 ml, 1.87 mMol) in anhydrous CH2Cl2 (2 ml.) is added dropwise over 10 min. to an ice-cold, stirring solution of p-nitrobenzyl 7α-azido-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate (0.65 g., 1.44 mMol) and Et3N (0.30 ml, 2.16 mMol) in anhydrous CH2Cl2 (10 ml.). After stirring 15 more min. in the cold, the solution is diluted with ice-cold CH2Cl2 (10 ml.), washed with ice-cold H2O (10 ml.), ice-cold 5% HCl (10 ml.), and ice-cold 5% NaHCO3 (10 ml.), dried with MgSO4, and filtered. Evaporation of the solvent in vacuo leaves p-nitrobenzyl 7α-azido-3-methanesulfonyloxy-3-acetoxymethyl-cepham-4-carboxylate.

Workup

  1. washwashed with ice-cold H2O (10 ml.), ice-cold 5% HCl (10 ml.), and ice-cold 5% NaHCO3 (10 ml.)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-bd7c2472c23945f3809a34f5af0d6436
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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