HRID2928

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7525

N-Ethylmorpholine

C6H13NO

HCID8784

Cinnamic acid

C9H8O2

结构：CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F

HCID151348

Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate

C12H22F6N6OP2

结构：COC(=O)Cn1c(C(=O)N[C@H](CCCCN)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21

HCID86752317

未命名化合物

PRODUCTS

生成物

结构：COC(=O)Cn1c(C(=O)N[C@H](CCCCNC(=O)C=Cc2ccccc2)C(=O)NCCCCCc2c(OC)cc(C)cc2OC)cc2ccccc21

HCID86752319

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: -5 °C

PROCEDURE

实验过程

0.87 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate, 0.645 g of BOP and 0.23 g of cinnamic acid are successively added to 30 ml of dimethylformamide. After cooling to -5° C., 0.26 g of N-ethylmorpholine is added under an inert atmosphere and the reaction mixture is maintained at 0° C. for 2 hours and is then left at room temperature for 18 hours. The reaction mixture is poured into a large volume of water and extraction is carried out with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residual oil is purified by flash chromatography on silica gel, eluent: CH2Cl2 /CH3OH 97/3 (v/v) in order to obtain methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(cinnamoylamino)pentyl}carbamoyl]indol-1-yl}acetate in the form of an oil.

WORKUP

后处理

temperaturethe reaction mixture is maintained at 0° C. for 2 hours
dry with materialThe organic extracts are dried over anhydrous sodium sulphate
customevaporated to dryness
customThe residual oil is purified by flash chromatography on silica gel, eluent

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-92a29c6b2fb348a4acb80711b9b5d5dc
来源数据集: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05731340
来源说明: uspto-grants-1998_03

反应 SMILES

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@H:20]([NH:26][C:27]([C:29]1[N:30]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[O:19].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:70](O)(=[O:79])[CH:71]=[CH:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.C(N1CCOCC1)C>C(OCC)(=O)C.O.CN(C)C=O>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C@H:20]([NH:26][C:27]([C:29]1[N:30]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:70](=[O:79])[CH:71]=[CH:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:19]