Triethylamine → HCID 131711147, compound

HRID 866480Notes

Reaction equation

HRID 866480 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]([C@H:9]1[C:31](=[O:32])[N:11]2[CH:12]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])[C:13]([OH:17])([CH3:16])[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:31](=[O:32])[N:11]2[CH:12]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=3)=[O:19])[C:13]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:16])[CH2:14][S:15][C@H:10]12)=[N+:7]=[N-:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131711148HCID 131711148, compound

Product 1

HCID 131711147HCID 131711147, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of CH3SO2Cl (34 μl, 0.44 mMol) in anhydrous CH2Cl2 (0.5 ml.) is added dropwise over 4 min. to an ice-cold, stirring solution of p-nitrobenzyl 7α-azido-3-hydroxy-3-methyl-cepham-4-carboxylate (135 mg., 0.34 mMol) and Et3N (71 μl, 0.51 mMol) in anhydrous CH2Cl2 (2 ml.). After stirring 15 more min. in the cold, the reaction mixture is diluted with cold CH2Cl2 (2 ml.), washed with ice-cold H2O (2 ml.), ice-cold 5% HCl (2 ml.), and ice-cold 5% NaHCO3 (2 ml.), dried over MgSO4, and filtered. Evaporation of the solvent in vacuo gives p-nitrobenzyl 7α-azido-3-methanesulfonyloxy-3-methyl-cepham-4-carboxylate (156 mg.) as a pale yellow oil: ir (CHCl3) 4.76, 5.62, 5.75, 6.57, 7.40, 8.47, and 11.1μ; nmr (CDCl3) δ2.10 (s, 3, CH3), 2.93 (s, 3, SO2CH3), 3.02 (d, l, J=14Hz, SCH), 3.87 (d, l, J=14Hz, SCH), 4.53 (d, l, J=1.2Hz, H7), 4.80 (s, l, H4), 4.97 (d, l, J=1.2Hz, H6), 5.35 (s, 2, CH2Ar), and 7.60, 8.28 (two d's 4, J=8.7Hz, ArH).

Workup

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

Sources & evidence

ORD record
ord-a1367c24a1004f78abf99d6d6e11fd13
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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