HRID1255525

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1140

Toluene

C7H8

反应SMILES：C=CCOc1cccc(O[C@@H]2C[C@@H](C(=O)OC)N(C(=O)OC(C)(C)C)C2)n1

HCID58158110

未命名化合物

PRODUCTS

产物

反应SMILES：C=CCn1c(O[C@@H]2C[C@@H](C(=O)OC)N(C(=O)OC(C)(C)C)C2)cccc1=O

HCID58158010

未命名化合物

收率 67%

AUXILIARIES

试剂、催化剂与溶剂

反应SMILES：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

An oven-dried 100 mL Kjeldahl Flask under nitrogen was charged with the product of Step 5 (2.82 g, 7.45 mmol) and toluene (15 ml). Degassed 5 minutes with nitrogen. Added tetrakis(triphenylphosphine)palladium(0) (0.431 g, 0.373 mmol). Heated in a 60° C. oil bath for 1 hour. HPLC/MS shows product. HPLC/MS looks good after 2 hours. Cooled. Evaporated. Subjected to flash column chromatography eluting with 99 methylene chloride/1 methanol. Evaporation of fractions containing product gave the title compound as an oil/foam. (1.91 g, 5.05 mmol, 67,7% yield). LCMS (ES+) m/z 379.3 (M+H)+.

WORKUP

后处理

customDegassed 5 minutes with nitrogen
temperatureCooled
customEvaporated
washeluting with 99 methylene chloride/1 methanol
customEvaporation of fractions
additioncontaining product

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-75dd4ad89d5a4c4f8f39de5123da125a
来源数据集: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08461107B2
来源说明: uspto-grants-2013_06

反应SMILES

C([O:4][C:5]1[N:10]=[C:9]([O:11][C@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)[CH:8]=[CH:7][CH:6]=1)C=C.[C:28]1(C)[CH:33]=CC=C[CH:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:33]([N:10]1[C:5](=[O:4])[CH:6]=[CH:7][CH:8]=[C:9]1[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1)[CH:28]=[CH2:29]