HRID1793832

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7616

Tripropylamine

C9H21N

HCID7656

Dibenzylamine

C14H15N

HCID199401

Phosphinic azide, diphenyl-

C12H10N3OP

结构：COc1ccc(S(=O)(=O)N2CC=CCC(C(=O)O)C2C(=O)OC(C)(C)C)cc1

HCID15550523

未命名化合物

PRODUCTS

生成物

结构：COc1ccc(S(=O)(=O)N2CC=CCC(NC(=O)N(Cc3ccccc3)Cc3ccccc3)C2C(=O)OC(C)(C)C)cc1

HCID12087866

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 75 °C

PROCEDURE

实验过程

The reaction is performed under an Argon blanket. 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 2-tert-butyl ester (204 mg, 0.5 mmol) is dissolved in 10 ml dry Dioxane. Tripropylamine (94 μl, 0.5 mmol) is added and then Diphenyl phosphoryl azide (DPPA). The reaction is heated to 75° C. for 5 h. After cooling to room temperature, Dibenzylamine (190.6 μl, 1 mmol) is added via syringe. The reaction is heated to 70° C. and stirred over night. Evaporation of the solvents and flash-chromatography, Hexane/Ethyl acetate (1:1) afforded the product: Cal. 606.8 found (M)+ 606.2.

WORKUP

后处理

temperatureAfter cooling to room temperature
temperatureThe reaction is heated to 70° C.
customEvaporation of the solvents and flash-chromatography, Hexane/Ethyl acetate (1:1)
customafforded the product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-99da9018331d4c898c6972eaa71da694
来源数据集: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07022690B2
来源说明: uspto-grants-2006_04

反应 SMILES

[C:1]([O:5][C:6]([CH:8]1[CH:14](C(O)=O)[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:32]([CH2:36]CC)CCC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH2:56]([NH:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>O1CCOCC1>[C:1]([O:5][C:6]([CH:8]1[CH:14]([NH:32][C:36]([N:63]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:46])[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:19])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]