HRID1422512

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15908

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

C8H17N3

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)OC(=O)CC[C@H](NC(=O)N[C@@H](CCCCN)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C

HCID25194225

1,5-Bis(1,1-dimethylethyl) N-[[[(1S)-5-amino-1-[(1,1-dimethylethoxy)carbonyl]pentyl]amino]carbonyl]-L-glutamate

C24H45N3O7

结构：C#CCOc1ccc(CN(CCCCCC(=O)O)Cc2nccn2CC(=O)OC(C)(C)C)cc1

HCID86676476

未命名化合物

PRODUCTS

生成物

结构：C#CCOc1ccc(CN(CCCCCC(=O)NCCCC[C@H](NC(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)Cc2nccn2CC(=O)OC(C)(C)C)cc1

HCID86676477

未命名化合物

收率 57.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID11

1,2-Dichloroethane

C2H4Cl2

PROCEDURE

实验过程

A solution of (S)-di-tert-butyl 2-(3-((S)-6-amino-1-(tert-butoxy)-1-oxohexan-2-yl)ureido)pentanedioate (0.480 g, 1.0 mmol), 6-(((1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid (0.220 g, 0.468 mmol), EDCI (0.191 g, 1.0 mmol), HOBt (0.135 g, 1.0 mmol) and DIPEA (0.40 mL) in DCE (10.0 mL) was stirred at room temperature for 3 h. The solvent was evaporated to give a residue, which was purified by Biotage eluting with DCM/MeOH to give (14S,18S)-tri-tert-butyl 1-(1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-(prop-2-yn-1-yloxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylate (0.251 g, 57%). MS (ESI), 939.5 (M+H)+.

WORKUP

后处理

customThe solvent was evaporated
customto give a residue, which
customwas purified by Biotage
washeluting with DCM/MeOH

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ee1e85950eaf4080bfc16e10826a8fac
来源数据集: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08926944B2
来源说明: uspto-grants-2015_01

反应 SMILES

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:14][C:15](=[O:34])[NH:16][C@@H:17]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:35]([O:39][C:40](=[O:68])[CH2:41][N:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH2:47][N:48]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64][CH2:65][C:66]#[CH:67])=[CH:60][CH:59]=1)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][C:54](O)=[O:55])([CH3:38])([CH3:37])[CH3:36].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCCCl>[C:35]([O:39][C:40](=[O:68])[CH2:41][N:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH2:47][N:48]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64][CH2:65][C:66]#[CH:67])=[CH:60][CH:59]=1)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][C:54](=[O:55])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[NH:14][C:15](=[O:34])[NH:16][C@H:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([CH3:36])([CH3:38])[CH3:37]