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

HRID 866481노트

반응식

HRID 866481 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebcc26ed02c144ccacc95072e984e771
출처 데이터셋
uspto-grants-1978_07
특허 번호
US04099000

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