HRID1048450

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID279800

Di-tert-butyl Iminodicarboxylate

C10H19NO4

HCID4622928

Cyanomethylenetributylphosphorane

C14H28NP

结构：CC[C@@H](CO)N1C(=O)[C@@](C)(CC(=O)OC)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1

HCID58573771

未命名化合物

PRODUCTS

生成物

结构：CC[C@@H](CN(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)N1C(=O)[C@@](C)(CC(=O)OC)C[C@H](c2cccc(Cl)c2)[C@H]1c1ccc(Cl)cc1

HCID67999215

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

A solution of methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetate (282 mg, 0.589 mmol; Example 186, Step A), 2-(tributylphosphoranylidene)acetonitrile (171 mg, 0.707 mmol) and di-tert-butyl iminodicarbonate (256 mg, 1.179 mmol) in toluene (3 mL) under argon was stirred at 110° C. for 2 h. Flash column purification on silica gel (0 to 60% EtOAc in hexanes) gave the title compound. Mass Spectrum (ESI) m/z=677 (M+1).

WORKUP

后处理

customFlash column purification on silica gel (0 to 60% EtOAc in hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a8b064ba09b14f468cb6fd2716111ddc
来源数据集: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08569341B2
来源说明: uspto-grants-2013_10

反应 SMILES

[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:24][CH3:25])[CH2:22]O)[C:11](=[O:26])[C@:10]([CH2:28][C:29]([O:31][CH3:32])=[O:30])([CH3:27])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(P(CCCC)(CCCC)=CC#N)CCC.[CH3:49][C:50]([O:53][C:54]([NH:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[O:55])([CH3:52])[CH3:51]>C1(C)C=CC=CC=1>[C:60]([O:59][C:57]([N:56]([C:54]([O:53][C:50]([CH3:52])([CH3:51])[CH3:49])=[O:55])[CH2:22][C@@H:21]([N:12]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:9][C@@:10]([CH2:28][C:29]([O:31][CH3:32])=[O:30])([CH3:27])[C:11]1=[O:26])[CH2:24][CH3:25])=[O:58])([CH3:63])([CH3:62])[CH3:61]