Triethylamine → HCID 131711144, compound

HRID 866477Notes

Reaction equation

HRID 866477 reaction equation
[N:1]([C@H:4]1[C:25](=[O:26])[N:6]2[CH:7]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])[C:8]([OH:12])([CH3:11])[CH2:9][S:10][C@H:5]12)=[N+:2]=[N-:3].CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[N:1]([C@H:4]1[C:25](=[O:26])[N:6]2[CH:7]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])[C:8]([O:12][S:35]([CH3:34])(=[O:37])=[O:36])([CH3:11])[CH2:9][S:10][C@H:5]12)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131711145HCID 131711145, compound

Product 1

HCID 131711144HCID 131711144, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-methoxybenzyl 7α-azido-3-hydroxy-3-methyl-cepham-4-carboxylate (310 mg., 0.82 mMol) and Et3N (1.72 μl, 1.23 mMol) in anhydrous CH2Cl2 (4 ml.) is cooled in an ice bath under N2. A solution of MeSO2Cl (83 μl, 1.07 mMol) in anhydrous CH2Cl2 (1 ml.) is added dropwise with stirring over 6 min. The resulting solution is stirred 15 more min. in the cold, then diluted with ice cold CH2Cl2 (5 ml.) and washed with ice cold H2O (5 ml.), 5% HCl (5 ml.), and 5% NaHCO3 (5 ml.). The CH2Cl2 solution is dried over MgSO4, filtered, and evaporated in vacuo to provide p-methoxybenzyl 7α-azido-3-methanesulfonyloxy-3-methyl-cepham-4-carboxylate (355 mg.) as a pale yellow gum: ir (CHCl3) 4.78, 5.63, 5.78, 6.64, 7.43, 7.99, 8.48, and 11.08μ; nmr (CDCl3) δ2.03 (s, 3, CH3), 2.68 (s, 3, SO2CH3), 3.00 (d, l, J=14Hz, SCH), 3.80 (s, 3, OCH3), 3.82 (d, l, J=14Hz, SCH), 4.47 (d, l, J=1.3Hz, H7), 4.65 (s, l, H4), 4.97 (d, l, J=1.3 Hz, H6), 5.00 and 5.28 (ABq, 2, J=10.5 Hz, CH2Ar), and 6.87 and 7.33 (two d's, 4, J=9Hz, ArH).

Workup

  1. stirringThe resulting solution is stirred 15 more min
  2. washwashed with ice cold H2O (5 ml.), 5% HCl (5 ml.), and 5% NaHCO3 (5 ml.)
  3. dry with materialThe CH2Cl2 solution is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-93ccd2a7b9264f918f5250481dd962c6
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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