HRID1532379

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID61186

Valeryl chloride

C5H9ClO

结构：Cc1cc(C)cc(-c2[nH]c3ccc(N)cc3c2CCN(Cc2ccccc2)C(=O)OC(C)(C)C)c1

HCID53723321

未命名化合物

PRODUCTS

生成物

结构：CCCCC(=O)Nc1ccc2[nH]c(-c3cc(C)cc(C)c3)c(CCN(Cc3ccccc3)C(=O)OC(C)(C)C)c2c1

HCID54425158

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8471

Triethylamine

C6H15N

PROCEDURE

实验过程

To a solution of {2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}benzylcarbamic acid tert-butyl ester (200 mg in 10 mL dry methylene chloride) at 0° C. was added 0.18 mL triethylamine followed by the dropwise addition of 0.06 mL valeryl chloride and the mixture stirred at low temperature. After 17 minutes, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed successively with saturated sodium bicarbonate and saturated ammonium chloride then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2) gave the title compound (230 mg).

WORKUP

后处理

customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
extractionextracted with ethyl acetate
washThe organic portion was washed successively with saturated sodium bicarbonate and saturated ammonium chloride
dry with materialthen dried over sodium sulfate
customPurification of the
concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cde92c1317444ef1855cadc4ec0a651c
来源数据集: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06200957B1
来源说明: uspto-grants-2001_03

反应 SMILES

[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH2:26])[CH:24]=2)[NH:19][C:18]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:36](Cl)(=[O:41])[CH2:37][CH2:38][CH2:39][CH3:40]>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:36](=[O:41])[CH2:37][CH2:38][CH2:39][CH3:40])[CH:24]=2)[NH:19][C:18]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)([CH3:4])([CH3:3])[CH3:2]