HRID1905108

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

结构：Cc1cc(SCC2=C(C(=O)OC(c3ccccc3)c3ccccc3)N3C(=O)[C@@H](N)[C@H]3SC2)n2nc(C(=O)OC(c3ccccc3)c3ccccc3)nc2n1

HCID13821813

未命名化合物

$结构：CC(=O)Oc1cc(C(=O)OC(c2ccccc2)c2ccccc2)c(CO/N=C(\C(=O)O)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1O$

HCID14479181

未命名化合物

PRODUCTS

生成物

$结构：CC(=O)Oc1cc(C(=O)OC(c2ccccc2)c2ccccc2)c(CO/N=C(\C(=O)N[C@@H]2C(=O)N3C(C(=O)OC(c4ccccc4)c4ccccc4)=C(CSc4cc(C)nc5nc(C(=O)OC(c6ccccc6)c6ccccc6)nn45)CS[C@H]23)c2csc(NC(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1O$

HCID16170823

未命名化合物

收率 14.7%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To an ice-cooled solution of the product obtained in Step 3 (0.63 g) and (6R,7R)-7-amino-3-[(2-diphenylmethyloxycarbonyl-5-methyl-s-triazolo[1,5-a]-pyrimidin-7-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[-4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (0.5 g) in dry dichloromethane (20 ml) was added dicyclohexylcarbodiimide (0.178 g), and the mixture was stirred overnight at room temperature. After filtering off the insoluble matters, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.15 g of the objective compound.

WORKUP

后处理

filtrationAfter filtering off the insoluble matters
concentrationthe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b93065a9fb624289b72dc20a05107891
来源数据集: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04840945
来源说明: uspto-grants-1989_06

反应 SMILES

[C:1]1([C:7]([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]3[CH:38]=[C:37]([OH:39])[C:36]([O:40][C:41](=[O:43])[CH3:42])=[CH:35][C:34]=3[C:44]([O:46][CH:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])/[C:27](O)=[O:28])[N:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:60]1([CH:66]([O:73][C:74]([C:76]2[N:77]3[C@H:80]([S:81][CH2:82][C:83]=2[CH2:84][S:85][C:86]2[N:91]4[N:92]=[C:93]([C:95]([O:97][CH:98]([C:105]5[CH:110]=[CH:109][CH:108]=[CH:107][CH:106]=5)[C:99]5[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=5)=[O:96])[N:94]=[C:90]4[N:89]=[C:88]([CH3:111])[CH:87]=2)[C@H:79]([NH2:112])[C:78]3=[O:113])=[O:75])[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:60]1([CH:66]([O:73][C:74]([C:76]2[N:77]3[C@H:80]([S:81][CH2:82][C:83]=2[CH2:84][S:85][C:86]2[N:91]4[N:92]=[C:93]([C:95]([O:97][CH:98]([C:105]5[CH:106]=[CH:107][CH:108]=[CH:109][CH:110]=5)[C:99]5[CH:100]=[CH:101][CH:102]=[CH:103][CH:104]=5)=[O:96])[N:94]=[C:90]4[N:89]=[C:88]([CH3:111])[CH:87]=2)[C@H:79]([NH:112][C:27](=[O:28])/[C:26](/[C:24]2[N:25]=[C:21]([NH:20][C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[S:22][CH:23]=2)=[N:30]\[O:31][CH2:32][C:33]2[CH:38]=[C:37]([OH:39])[C:36]([O:40][C:41](=[O:43])[CH3:42])=[CH:35][C:34]=2[C:44]([O:46][CH:47]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)=[O:45])[C:78]3=[O:113])=[O:75])[C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1