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

HRID 1632875

反应方程式

HRID 1632875 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(C2N=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].[C:46]([NH:49][CH2:50][CH2:51][SH:52])(=[O:48])[CH3:47].O.[OH-].[Na+]>ClCCl.[Cl-].C([N+](C)(C)CCCCCCCCCCCCCCCC)C1C=CC=CC=1>[C:46]([NH:49][CH2:50][CH2:51][S:52][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:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:45][CH:44]=2)=[O:11])[CH3:14])[C:19]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)=[O:24])(=[O:48])[CH3:47]

参与物

7

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 14484N-乙酰基半胱胺HCID 14798二甲基对苯二胺二盐酸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 131713936p-Nitrobenzyl (5RS,6SR)-3-(2-acetamidoethylthio)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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2 次

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 (15 mg) in dichloromethane (2 ml) was cooled in an ice-bath and treated with benzyldimethyl-n-hexadecylammonium chloride (1.1 mg), followed by 2-acetamidoethanethiol (3 mg) in dichloromethane (1 ml), followed by water (1 ml), followed by 0.1M aqueous NaOH (0.25 ml). After stirring in the cold for 30 min. the reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. After dilution with CH2Cl2 /H2O and separation, the dichloromethane layer was dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate, followed by ethylacetate/ethanol (95:5) to give the title compound νmax. (CH2Cl2) 3450, 1790, 1750, 1700(sh), 1680, 1525, 1350 cm-1.

后处理

  1. stirringstirred for 1.5 h
  2. customAfter dilution with CH2Cl2 /H2O and separation
  3. dry with materialthe dichloromethane layer was dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with ethyl acetate

来源与证据

ORD记录
ord-d5695a4712ae4600a10a132b09ae61bf
来源数据集
uspto-grants-1984_10
专利号
US04477662

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