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

HRID 866481Notes

Reaction equation

HRID 866481 reaction equation
[OH:1][C:2]1([CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH2:7][S:6][CH:5]=[N:4][CH:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:9].CCN(CC)CC.[N:33]([CH2:36][C:37](Cl)=[O:38])=[N+:34]=[N-:35]>C(Cl)Cl>[N:33]([C@H:36]1[C:37](=[O:38])[N:4]2[CH:3]([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)=[O:9])[C:2]([OH:1])([CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH2:7][S:6][C@H:5]12)=[N+:34]=[N-:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109095582-azidoacetyl ChlorideHCID 20321415p-Nitrobenzyl 5-hydroxy-5-acetoxymethyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate

Product 1

HCID 86735841p-Nitrobenzyl 7alpha-azido-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Nitrobenzyl 5-hydroxy-5-acetoxymethyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (1.27 g., 3.45 mMol) and Et3N (0.58 ml., 4.16 mMol) in anhydrous CH2Cl2 (50 ml.) is stirred under a N2 atomsphere at room temperature while a solution of N3CH2COCl (0.36 ml., 4.13 mMol) in anhydrous CH2Cl2 (20 ml.) is added dropwise over 90 min. After stirring 30 more min., the solution is washed twice with H2O and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residual oil us chromatographed on a column of Baker silica gel. Elution with 3:1 PhH-EtOAc yields p-nitrobenzyl 7α-azido-3-hydroxy-3-acetoxymethyl-cepham-4-carboxylate.

Workup

  1. additionis added dropwise over 90 min
  2. wash, the solution is washed twice with H2O and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residual oil us chromatographed on a column of Baker silica gel
  7. washElution with 3:1 PhH-EtOAc

Sources & evidence

ORD record
ord-ebcc26ed02c144ccacc95072e984e771
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

Loading…