Triethylamine → HCID 86735542, compound

HRID 1679187Notes

Reaction equation

HRID 1679187 reaction equation
[N:1]([CH:4]1[C:30](=[O:31])[N:6]2[CH:7]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[C:8]([CH2:12][O:13][C:14](=[O:16])[CH3:15])([OH:11])[CH2:9][S:10][C@:5]12[S:32][CH3:33])=[N+:2]=[N-:3].CCN(CC)CC.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[N:1]([CH:4]1[C:30](=[O:31])[N:6]2[CH:7]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[C:8]([CH2:12][O:13][C:14](=[O:16])[CH3:15])([O:11][S:42]([CH3:41])(=[O:44])=[O:43])[CH2:9][S:10][C@:5]12[S:32][CH3:33])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86735541HCID 86735541, compound

Product 1

HCID 86735542HCID 86735542, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold, stirring solution of p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethyl-3-hydroxy-cepham-4-carboxylate (2.72 g., 5.47 mMol) and Et3N (1.15 ml., 8.25 mMol) in anhydrous CH2Cl2 (20 ml.) is added dropwise a solution of methanesulfonyl chloride (0.51 ml., 6.56 mMol) in anhydrous CH2Cl2 (15 ml.). After stirring 15 more mins. in the cold, the solution is washed with H2O, 5% HCl, 5% NaHCO3, and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residual oil is crystallized from CH2Cl2 --MeOh to afford p-nitrobenzyl 7-azido-6-methylthio-3-acetoxymethyl-3-methylsulfonyloxycepham-4-carboxylate (2.15 g.) as yellow crystals: mp 147° C.; ir (CHCl3) 4.72, 5.59, 5.71, 6.58 and 7.42μ; nmr (CDCl3)δ 2.17 (s, 3, COCH3), 2.20 (s, 3, SCH3), 3.00 (s, 3, SO2CH3), 3.22, 4.28 (ABq, 2, J=14Hz, SCH2, 4.67, 4.95 (ABq, 2, J=13Hz, CH2OAc), 4.88 (s, 1, H7), 5.20 (s, 1, H4), 5.35 (s, 2, CH2Ar), and 7.63, 8.25 (ABq, 4, J=9, ArH).

Workup

  1. washin the cold, the solution is washed with H2O, 5% HCl, 5% NaHCO3, and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residual oil is crystallized from CH2Cl2

Sources & evidence

ORD record
ord-d09482aee2a34bb8a1cc87919c105f5d
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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