HRID56872

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2337

Benzocaine

C9H11NO2

HCID12734

Diisopropylcarbodiimide

C7H14N2

结构：COc1cn(C(CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N

HCID123912396

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)c1ccc(NC(=O)C(CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)n2cc(OC)c(-c3cc(Cl)ccc3C#N)cc2=O)cc1

HCID123769555

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

565 mg (940 μmol) of 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate), 155 mg (940 μmol) of ethyl 4-aminobenzoate, 134 mg (940 μmol) of Oxima and 146 μl (940 μmol) of DIC in 19 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient). Yield: 268 mg (38% of theory)

WORKUP

后处理

customThe crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f6f9939b854d48d2b32ebb7d2acb3c4c
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09434690B2
来源说明: uspto-grants-2016_09

反应 SMILES

[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:27][C:26]1=[O:42])[C:22]([OH:24])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:43][C:44]1[CH:54]=[CH:53][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:27][C:26]1=[O:42])[C:22]([NH:43][C:44]1[CH:45]=[CH:46][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:53][CH:54]=1)=[O:24])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1