HRID1852126

反应详情

EQUATION

反应方程式

REACTANTS

反应物

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)OC)C[C@H]1C=C

HCID89541288

未命名化合物

PRODUCTS

生成物

$结构：COC(=O)[C@@]12C[C@H]1/C=C\CCC(C)C[C@@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](O)C[C@H]1C(=O)N2$

HCID71005125

未命名化合物

收率 82.7%

AUXILIARIES

试剂、催化剂与溶剂

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

溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

A solution of (1R,2S)-methyl 1-((2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate (2.68 g, 5 mmol) in DCE (600 mL) was sparged with nitrogen for 30 min. and then Hoveyda-Grubbs Catalyst 2nd Generation (0.189 g, 0.300 mmol) was added and the reaction heated to 80° C. for 2 hrs. The reaction was concentrated and purified by flash chromatography on silica gel (20-60% Acetone in hexanes) to give 2.1 g of the product (2R,6S,7R,13aS,14aR,16aS,Z)-methyl 6-((tert-butoxycarbonyl)amino)-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]diazacyclopentadecine-14a-carboxylate. MS: MS m/z 530.18 (M++23).

WORKUP

后处理

concentrationThe reaction was concentrated
custompurified by flash chromatography on silica gel (20-60% Acetone in hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-60b982b372b14418bcd21c44dc75d356
来源数据集: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08957203B2
来源说明: uspto-grants-2015_02

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:30]([CH3:38])[CH2:31][CH:32]([CH3:37])[CH2:33][CH2:34]C=C)[C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]1[C:18]([NH:20][C@:21]1([C:26]([O:28][CH3:29])=[O:27])[CH2:23][C@H:22]1[CH:24]=[CH2:25])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:10](=[O:11])[N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[C:18](=[O:19])[NH:20][C@:21]2([C:26]([O:28][CH3:29])=[O:27])[CH2:23][C@H:22]2[CH:24]=[CH:25][CH2:34][CH2:33][CH:32]([CH3:37])[CH2:31][C@H:30]1[CH3:38])=[O:7])([CH3:3])([CH3:2])[CH3:4]