HRID1177637

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID176

Acetic Acid

C2H4O2

结构：Nc1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1

HCID57403052

未命名化合物

HCID86597499

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N[C@H](CC(=O)O)C(=O)Nc1ccc(-c2nc3ccc(C4(c5ccccc5)CC4)nc3s2)c(F)c1

HCID67111578

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID241

Benzene

C6H6

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine (206 mg, 0.570 mmol) and (R)-tert-butyl 2,5-dioxo-tetrahydrofuran-3-ylcarbamate (123 mg, 0.570 mmol) was added benzene (5.7 mL) and acetic acid (163 μl, 2.85 mmol) before it was stirred at 80° C. for 1 h. The two regioisomers were separated via SFC (Column: Princeton Pyridine, Mobile Phase: 60:40 liquid CO2/MeOH) to give (3R)-3-(tert-butoxycarbonylamino)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoic acid and its regioisomer. MS (ESI) m/z: Calculated: 576.2; Observed: 577.1 (M++H).

WORKUP

后处理

customThe two regioisomers were separated via SFC (Column: Princeton Pyridine, Mobile Phase: 60:40 liquid CO2/MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-819a09bc986e43bebea2680b06368edb
来源数据集: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07842685B2
来源说明: uspto-grants-2010_11

反应 SMILES

[F:1][C:2]1[CH:3]=[C:4]([NH2:26])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[O:27]=[C:28]1[C@H:32]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][C:30](=[O:41])[O:29]1.C(O)(=O)C>C1C=CC=CC=1>[C:36]([O:35][C:34]([NH:33][C@@H:32]([C:28]([NH:26][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:18][CH2:19]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1)=[O:27])[CH2:31][C:30]([OH:41])=[O:29])=[O:40])([CH3:38])([CH3:39])[CH3:37]