HRID1397123

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7922

Succinic anhydride

C4H4O3

反应SMILES：CC(C)(C)OC(=O)CCC(N)(CCC(=O)OC(C)(C)C)CCC(=O)OC(C)(C)C

HCID10927842

AMINOTRIESTER

C22H41NO6

PRODUCTS

产物

反应SMILES：CC(C)(C)OC(=O)CCC(CCC(=O)OC(C)(C)C)(CCC(=O)OC(C)(C)C)NC(=O)CCC(=O)O

HCID86666536

未命名化合物

收率 64.2%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of amine 72 (513 mg, 1.23 mmol) in CH2Cl2 (6.2 mL) was added succinic anhydride (135 mg, 1.35 mmol) and DMAP (8 mg, 0.062 mmol). The mixture was stirred for 6 h 15 min and concentrated to dryness. The crude product was purified by flash chromatography on a Biotage™ flash chromatography system, using a gradient of 50-100% EtOAc in CH2Cl2 as eluent to yield acid 73 (407 mg, 64%) as a white foam: 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 27H), 1.97-2.01 (m, 6H), 2.23-2.26 (m, 6H), 2.47-2.51 (m, 2H), 2.65-2.68 (m, 2H), 6.83 (s, 1H).

WORKUP

后处理

concentrationconcentrated to dryness
customThe crude product was purified by flash chromatography on a Biotage™ flash chromatography system

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-21a9f2f9aa6e4bac9c5ef545a37669a5
来源数据集: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08901072B2
来源说明: uspto-grants-2014_12

反应SMILES

[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH2:29])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]([NH:29][C:30]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:36])([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]