HRID20058

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@H]1CO1

HCID9903372

(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

C15H21NO3

HCID67305954

未命名化合物

PRODUCTS

生成物

HCID6422

未命名化合物

结构：CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CN[C@H]1CC(C)(C(F)(F)F)Oc2ccc(Br)cc21

HCID86614140

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 mixture of (4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine (179 mg, 577 μmol) and tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (198 mg, 750 μmol) in ethanol was heated at reflux for 16 h. At this point, there was still the starting amine left. An additional 1.3 eq of epoxide was added to the reaction, and continued to reflux for 6 h. The resulted mixture was concentrated and purified on Shimadzu HPLC to afford the title compound as a TFA salt. MS m/z: 573, 575.

WORKUP

后处理

temperaturewas heated
temperatureat reflux for 16 h
waitleft
temperatureto reflux for 6 h
concentrationThe resulted mixture was concentrated
custompurified on Shimadzu HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0737efb85022439ba9ec17ec97424d0a
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07745484B2

反应 SMILES

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