HRID230041

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N(C(C(=O)OCc2ccc([N+](=O)[O-])cc2)=P(c2ccccc2)(c2ccccc2)c2ccccc2)[C@@H]1[C@@H](C)C(=O)c1cn2cnc(C(=O)c3cccnc3)c2s1

HCID86619389

未命名化合物

PRODUCTS

生成物

结构：C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(c3cn4cnc(C(=O)c5cccnc5)c4s3)[C@H](C)[C@H]12

HCID131727433

未命名化合物

收率 72.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

A solution of 54.6 mg of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)methyl]azetidin-2-one in 2 ml of toluene was heated under reflux for 2.5 hr. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 5% methanol/ethyl acetate) to give 28.3 mg of (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate.

WORKUP

后处理

temperatureunder reflux for 2.5 hr
customThe solvent was removed by evaporation
customthe residue was purified by thin layer chromatography (developed with 5% methanol/ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ac7be182452745c3ad1ba7457e4d4cc2
来源数据集: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07563901B2
来源说明: uspto-grants-2009_07

反应 SMILES

[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:34])[C:16]([C:18]2[S:22][C:21]3=[C:23]([C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[N:24]=[CH:25][N:20]3[CH:19]=2)=O)[N:13]([C:35]([C:55]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=2)=[O:56])=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:12]1=[O:68])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:68])[N:13]2[C:35]([C:55]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=3)=[O:56])=[C:16]([C:18]3[S:22][C:21]4=[C:23]([C:26]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[O:27])[N:24]=[CH:25][N:20]4[CH:19]=3)[C@H:15]([CH3:34])[C@H:14]12)[CH3:10])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]