HRID1397602

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6195

1-Naphthaldehyde

C11H8O

HCID656671

Sodium metabisulfite

Na2O5S2

结构：CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@@H](Oc2ccnc(N)c2N)C[C@@H]1O[Si](C)(C)C(C)(C)C

HCID66797960

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@@H](Oc2ccnc3[nH]c(-c4cccc5ccccc45)nc23)C[C@@H]1O[Si](C)(C)C(C)(C)C

HCID178455232

未命名化合物

收率 68%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

A mixture of 1-naphthalenecarboxaldehyde (115 mg, 0.000738 mol), 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclo pentyl]oxy}pyridine-2,3-diamine (115.1 mg, 0.0002460 mol) and sodium metabisulfite (0.140 g, 0.000738 mol) in acetonitrile (2.00 mL) was subject to microwave irradiation at 180° C. for 25 mins. The mixture was filtered and the filtrate was concentrated. The residue was purified by preparative plate chromatography (25% EtOAc/hexanes) to afford the title compound (0.101 g, 68%) as a white solid.

WORKUP

后处理

customirradiation at 180° C. for 25 mins
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe residue was purified by preparative plate chromatography (25% EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9103b0f3300d4f5c88c70181fa3f254a
来源数据集: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08901136B2
来源说明: uspto-grants-2014_12

反应 SMILES

[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Si:13]([O:20][C@@H:21]1[C@H:25]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@@H:23]([O:35][C:36]2[CH:41]=[CH:40][N:39]=[C:38]([NH2:42])[C:37]=2[NH2:43])[CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[Si:13]([O:20][C@@H:21]1[C@H:25]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@@H:23]([O:35][C:36]2[CH:41]=[CH:40][N:39]=[C:38]3[NH:42][C:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)=[N:43][C:37]=23)[CH2:22]1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]