聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → p-Nitrobenzyl(5RS,6SR)-3-[(Z)-2-Acetamidoethenylthio]-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1632870

反应方程式

HRID 1632870 反应方程式
[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([CH2:8][O:9][C:10]([O:12][CH:13]([CH:15]2[C:21](=[O:22])[N:20]3[CH:16]2[CH2:17][C:18]([S:36]([C:38]2N=CC=CN=2)=O)=[C:19]3[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH2:46]>ClCCl.[Cl-].C([N+](C)(C)CCCCCCCCCCCCCCCC)C1C=CC=CC=1>[C:19]([NH:20]/[CH:16]=[CH:38]\[S:36][C:18]1[CH2:17][CH:16]2[N:20]([C:21](=[O:22])[CH:15]2[CH:13]([O:12][C:10]([O:9][CH2:8][C:7]2[CH:44]=[CH:45][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[CH3:14])[C:19]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:46])[CH3:18]

参与物

5

反应物 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 20442568p-Nitrobenzyl(5RS,6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

产物 1

HCID 88723757p-Nitrobenzyl(5RS,6SR)-3-[(Z)-2-Acetamidoethenylthio]-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate收率 52%

试剂、催化剂与溶剂 2

HCID 31202N-十六烷基-N,N-二甲基苄基氯化铵催化剂HCID 6344二氯甲烷溶剂

实验过程

p-Nitrobenzyl(5RS,6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (230 mg) in dichloromethane (25 ml) was treated with benzyldimethyl-n-hexadecylammonium chloride (12 mg), cooled in an ice-bath, and treated with sodium Z-2-acetamidoethenylthiolate (contanimated by 1 molar equivalent NaCl) (77 mg) in water (25 ml). After stirring vigorously for 25 min. the layers were separated, and the dichloromethane layer was washed with dilute aqueous NaHCO3, followed by brine. After drying (MgSO4) the solution was evaporated in vacuo and the residue was chromatographed on silica gel (230-400 mesh ASTM), eluting with ethyl acetate to give the title compound (118 mg, 52% yield).

后处理

  1. temperaturecooled in an ice-bath
  2. customwere separated
  3. washthe dichloromethane layer was washed with dilute aqueous NaHCO3
  4. dry with materialAfter drying (MgSO4) the solution
  5. customwas evaporated in vacuo
  6. customthe residue was chromatographed on silica gel (230-400 mesh ASTM)
  7. washeluting with ethyl acetate

来源与证据

ORD记录
ord-eae508a9ffc14ede9bea75e958bd22a6
来源数据集
uspto-grants-1984_10
专利号
US04477662

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