HRID661055

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID67184

1-Bromopyrrolidine-2,5-dione

C4H4BrNO2

结构：CC(C)(O)C#Cc1csc(N(C[C@H](Cc2ccc(C(F)(F)F)cc2)NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)n1

HCID57634169

未命名化合物

PRODUCTS

生成物

结构：CC(C)(O)C#Cc1nc(N(C[C@H](Cc2ccc(C(F)(F)F)cc2)NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)sc1Br

HCID57634127

未命名化合物

收率 24.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID5943

Carbon tetrachloride

CCl4

PROCEDURE

实验过程

(S)-tert-butyl 1-(N-(4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.18 g, 0.31 mmol) was taken up in 5 mL of CCl4 and NBS (0.11 g, 0.62 mmol) was added. After 3 hours, the solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (5% to 40% EtOAc/hexanes) to afford (S)-tert-butyl 1-(N-(5-bromo-4-(3-hydroxy-3-methylbut-1-ynyl)thiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.05 g, 24% yield) as a white solid.

WORKUP

后处理

customthe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography on silica gel (5% to 40% EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-754a9e78e37c4512a4c752c8bbe60238
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08084479B2
来源说明: uspto-grants-2011_12

反应 SMILES

[OH:1][C:2]([CH3:40])([CH3:39])[C:3]#[C:4][C:5]1[N:6]=[C:7]([N:10]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11][C@@H:12]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:8][CH:9]=1.C1C(=O)N([Br:48])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:48][C:9]1[S:8][C:7]([N:10]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:11][C@@H:12]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[N:6][C:5]=1[C:4]#[C:3][C:2]([OH:1])([CH3:40])[CH3:39]