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

HRID 866481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866481
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ebcc26ed02c144ccacc95072e984e771
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04099000

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