huagongshe.com
HRID1852124

反应详情

EQUATION

反应方程式

HRID 1852124 的结构方程式

REACTANTS

反应物

1
结构：C=CCCC(C)C[C@@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C
HCID89550268

未命名化合物

PRODUCTS

生成物

1
结构：CC1CC/C=C\[C@@H]2C[C@@]2(C(=O)NS(=O)(=O)C2CC2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)OC(C)(C)C)[C@H](C)C1
HCID89550183

未命名化合物

收率 77.1%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：Cc1cc(C)c(N2CCN(c3c(C)cc(C)cc3C)[C]2=[Ru]([Cl])([Cl])=[CH]c2ccccc2OC(C)C)c(C)c1
催化剂HCID11763533

[1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene](dichloro)({2-[(propan-2-yl)oxy]phenyl}methylidene)ruthenium

C31H38Cl2N2ORu

结构：ClCCCl
溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

CONDITIONS

反应条件

温度
80 °C

PROCEDURE

实验过程

A solution of tert-butyl ((2S,3R)-1-((2S,4R)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate (9.5 g, 15.21 mmol) in DCE (2500 ml) was sparged with nitrogen for 30 min. and then Hoveyda-Grubbs Catalyst 2nd Generation (0.574 g, 0.912 mmol) was added and the reaction heated to 80° C. for 2 hrs then cooled down to 45° C. and stirred for 2 days. The reaction was concentrated and purified by flash chromatography on silica gel (20-60% Acetone in hexanes) to give the product tert-Butyl((2R,6S,7R,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-hydroxy-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (7 g). MS: MS m/z 597.35 (M++1).

WORKUP

后处理

  1. temperaturethen cooled down to 45° C.
  2. concentrationThe reaction was concentrated
  3. custompurified by flash chromatography on silica gel (20-60% Acetone in hexanes)