HRID253598

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID123227

3-Cyclobutene-1,2-dione, 3,4-dimethoxy-

C6H6O4

结构：C[Si](C)(C)CCOC(=O)N(Cc1ccc(C#N)cc1)C[C@@H](O)[C@@H](N)CC1CCCCC1

HCID66861734

未命名化合物

PRODUCTS

生成物

结构：COc1c(N[C@@H](CC2CCCCC2)[C@H](O)CN(Cc2ccc(C#N)cc2)C(=O)OCC[Si](C)(C)C)c(=O)c1=O

HCID86632800

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A solution of (2R,3S)-1-(N-(4-cyanobenzyl)-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-2-hydroxy-3-amino-4-cyclohexylbutane (764 mg, 1.68 mmol) in EtOH (20 mL) was treated with 3,4-dimethoxycyclobut-3-ene-1,2-dione (300 mg, 2.10 mmol, 1.25 equiv) and Et3N (212 mg, 1.25 equiv). The resulting solution was allowed to stir at rt for 17 h. The excess 3,4-dimethoxycyclobut-3-ene-1,2-dione was removed by flash chromatography on silica gel, eluting with 0-65% EtOAc in hexanes. Analysis of the compound by LC-MS showed that it was of sufficient purity to employ in the subsequent steps.

WORKUP

后处理

customThe excess 3,4-dimethoxycyclobut-3-ene-1,2-dione was removed by flash chromatography on silica gel
washeluting with 0-65% EtOAc in hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f3a06eccc2fa4bc788578fc76fb70eb3
来源数据集: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07872028B2
来源说明: uspto-grants-2011_01

反应 SMILES

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