HRID723218

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID73916

Methyl 4-chloroformylbutyrate

C6H9ClO3

结构：CCOC(=O)CCCCCNC(=O)Nc1cc(C)c(-c2cccc(S(=O)(=O)c3cc(C(=N)NC(=O)OC(C)(C)C)sc3SC)c2)c(N)c1

HCID145857638

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)CCCCCNC(=O)Nc1cc(C)c(-c2cccc(S(=O)(=O)c3cc(C(=N)NC(=O)OC(C)(C)C)sc3SC)c2)c(NC(=O)CCCC(=O)OC)c1

HCID145857701

未命名化合物

收率 55.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

4-Chlorocarbonyl-butyric acid methyl ester (20.4 μL, 0.148 mmol) was added to a solution of 6-(3-{2-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-ureido)-hexanoic acid ethyl ester (70.8 mg, 96.4 μmol, Example 278: step c) and triethylamine (41.2 μL, 0.296 mmol) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight at rt, then diluted in EtOAc, washed with water and brine, and dried over magnesium sulfate. Removal of solvents in vacuo followed by flash chromatography (75–100% EtOAc/hexanes) yielded the title compound as a brown oil (45.5 mg, 54.5%). ESI-MS (m/z): Calcd. for C39H51N5O10S3: 846.3 (M+1); found: 845.9.

WORKUP

后处理

washwashed with water and brine
dry with materialdried over magnesium sulfate
customRemoval of solvents in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-dd127ed0e4ab40fcbcc2a9b73dc38a58
来源数据集: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07138530B2
来源说明: uspto-grants-2006_11

反应 SMILES

[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[CH2:11]([O:13][C:14](=[O:58])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([S:37]([C:40]3[CH:44]=[C:43]([C:45]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[NH:46])[S:42][C:41]=3[S:55][CH3:56])(=[O:39])=[O:38])[CH:32]=2)=[C:26]([NH2:57])[CH:25]=1)=[O:22])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[CH2:11]([O:13][C:14](=[O:58])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH:23][C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([S:37]([C:40]3[CH:44]=[C:43]([C:45]([NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])=[NH:46])[S:42][C:41]=3[S:55][CH3:56])(=[O:39])=[O:38])[CH:32]=2)=[C:26]([NH:57][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:10])[CH:25]=1)=[O:22])[CH3:12]