HRID1908644

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID79040

Propanoic acid, 2-bromo-, ethyl ester

C5H9BrO2

结构：CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)c2cc(O)n(-c3ccccc3)n2)CC1

HCID178473388

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2cc(OC(C)C(=O)O)n(-c3ccccc3)n2)CC1

HCID66854774

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a solution of 1.50 g 4-{(S)-4-tert-butoxycarbonyl-2-[(5-hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 12 ml DMF were added 670 μl ethyl 2-bromopropionate and 3.2 g cesium carbonate. After stirring at RT for 24 h the solution was diluted with ethyl acetate and extracted with aqueous LiCl (4% w/w). The crude product obtained after evaporation of the solvent was dissolved in THF and treated with 1 N NaOH. When conversion was complete (4 h) Amberlite IR-120® was added, the suspension filtrated and the filtrate evaporated to give the crude product (1.56 g)

WORKUP

后处理

extractionextracted with aqueous LiCl (4% w/w)
customThe crude product obtained
customafter evaporation of the solvent
dissolutionwas dissolved in THF
additiontreated with 1 N NaOH
custom(4 h) Amberlite IR-120®
additionwas added
filtrationthe suspension filtrated
customthe filtrate evaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a923d9f09cae463685ad30a85032b298
来源数据集: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08598179B2
来源说明: uspto-grants-2013_12

反应 SMILES

[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([OH:31])[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH:40]([CH3:46])[C:41]([O:43]CC)=[O:42].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH:40]([C:41]([OH:43])=[O:42])[CH3:46])[N:28]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]