HRID2242429

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID5363146

Diisopropyl azodicarboxylate

C8H14N2O4

结构：CCC[C@H](NC(=O)[C@@H]1C[C@H](O)C[C@H]1C(=O)OC)C(=O)OC(C)(C)C

HCID59204201

未命名化合物

HCID178487676

未命名化合物

PRODUCTS

生成物

结构：CCC[C@H](NC(=O)[C@@H]1C[C@@H](Oc2cc(-c3ccccc3)nc3cc(OC)ccc23)C[C@H]1C(=O)OC)C(=O)OC(C)(C)C

HCID59204183

未命名化合物

收率 78%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

Compound 42 (249 mg, 0.725 mmol), 2-phenyl-7-methoxy-4-quinolinol (310 mg, 1.23 mmol) and PPh3 (580 mg, 2.21 mmol) were dissolved in dry THF and the temperature was lowered to 0° C. DIAD (435 uL. 2.21 mmol) dissolved in 2 mL dry THF, was added to the mixture during five minutes. After two hours the temperature was raised to room temperature and the solution was stirred overnight. Evaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1) gave 43 (324 mg, 78%).

WORKUP

后处理

customwas lowered to 0° C
additionwas added to the mixture during five minutes
customEvaporation and purification by flash column chromatography (toluene/EtOAc gradient 6:1 to 4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1f2e49f2e14d4746ba744ccbcd5ad068
来源数据集: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07671032B2
来源说明: uspto-grants-2010_03

反应 SMILES

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][C@H:6]1[C:11](=[O:24])[NH:12][C@H:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][CH3:16])=[O:4].[C:25]1([C:31]2[CH:40]=[C:39](O)[C:38]3[C:33](=[CH:34][C:35]([O:42][CH3:43])=[CH:36][CH:37]=3)[N:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][C:39]2[C:38]3[C:33](=[CH:34][C:35]([O:42][CH3:43])=[CH:36][CH:37]=3)[N:32]=[C:31]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:40]=2)[CH2:7][C@H:6]1[C:11](=[O:24])[NH:12][C@H:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][CH3:16])=[O:4]