HRID71955

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID517165

Ammonium acetate

C2H7NO2

结构：COC(=O)NC(C(=O)N1CC2(CC2)CC1c1nc(-c2ccc3cc(-c4ccc(C(=O)CNC(=O)C5SCCN5C(=O)OC(C)(C)C)cc4)ccc3c2)c[nH]1)C(C)C

HCID178502143

未命名化合物

PRODUCTS

生成物

结构：COC(=O)NC(C(=O)N1CC2(CC2)CC1c1nc(-c2ccc3cc(-c4ccc(-c5cnc(C6SCCN6C(=O)OC(C)(C)C)[nH]5)cc4)ccc3c2)c[nH]1)C(C)C

HCID178502142

未命名化合物

收率 44.3%

CONDITIONS

反应条件

温度: 135 °C

PROCEDURE

实验过程

2-{2-[4-(6-{2-[5-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-1H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-2-oxo-ethylcarbamoyl}-thiazolidine-3-carboxylic acid tert-butyl ester (350 mg, 0.44 mmol) was dissolved in m-xylenes (3.0 mL) and heated at 135° C. Solid ammonium acetate (400 mg, 9.07 mmol) was added and the reaction was stirred at 135° C. After 45 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude reaction product was partitioned between chloroform and water. The organic layer was collected and dried over sodium sulfate. Filtration and evaporation of solvents gave the crude product. The crude material was purified via silica gel chromatography (eluent: EtOAc/hexanes) to yield the product (151.3 mg, 0.195 mmol).

WORKUP

后处理

temperaturethe reaction was cooled to room temperature
customthe volatiles were removed in vacuo
customThe crude reaction product
customwas partitioned between chloroform and water
customThe organic layer was collected
dry with materialdried over sodium sulfate
filtrationFiltration and evaporation of solvents
customgave the crude product
customThe crude material was purified via silica gel chromatography (eluent: EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bbeead2c746147e1952938422fd9a6d5
来源数据集: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08822430B2
来源说明: uspto-grants-2014_09

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13](=O)[NH:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:34]4[N:35]=[C:36]([CH:39]5[CH2:45][C:42]6([CH2:44][CH2:43]6)[CH2:41][N:40]5[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])[NH:37][CH:38]=4)[CH:30]=3)[CH:25]=2)=[CH:20][CH:19]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:62]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]1[NH:62][C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:34]5[N:35]=[C:36]([CH:39]6[CH2:45][C:42]7([CH2:43][CH2:44]7)[CH2:41][N:40]6[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])[NH:37][CH:38]=5)[CH:30]=4)[CH:25]=3)=[CH:22][CH:23]=2)=[CH:15][N:14]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]