HRID465422

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID217242

2-Amino-1-(4-amino-3,5-dichlorophenyl)ethan-1-ol

C8H10Cl2N2O

HCID5003444

Sodium cyanotrihydroborate

CH3BNNa

HCID5360545

Sodium

HCID54723367

未命名化合物

PRODUCTS

生成物

结构：CC(Cc1ccc(OC2=C(O)C(=O)NC2=O)cc1)NCC(O)c1cc(Cl)c(N)c(Cl)c1.CC(Cc1ccc(OC2=C(O)C(=O)NC2=O)cc1)NCC(O)c1cc(Cl)c(N)c(Cl)c1.O

HCID88474232

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of the sodium salt of 4-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione (1.41 g) and 2-(4-amino-3,5-dichlorophenyl)-2-hydroxy ethylamine (1.0 g) in methanol was treated with sodium cyanoborohydride (0.35 g) and stirred at ambient temperature for 18 hours. The solvent was removed in vacuo, the residue dissolved in acetone and purified by column chromatography on silica using acetone as eluent followed by methanol after the elution of fast-running impurities. The solid obtained was washed with acetone and filtered to give 4-[4-[2-[(4-amino-3,5-dichloro-β-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione hemihydrate as a (34:66) mixture of diastereoisomers.

WORKUP

后处理

customThe solvent was removed in vacuo
dissolutionthe residue dissolved in acetone
custompurified by column chromatography on silica
washafter the elution of fast-running impurities
customThe solid obtained
washwas washed with acetone
filtrationfiltered

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7ebc169d52534cc09da67ca9d4c7f19b
来源数据集: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05153210
来源说明: uspto-grants-1992_10

反应 SMILES

[Na].[CH2:2]([C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=2[OH:18])=[CH:8][CH:7]=1)[C:3]([CH3:5])=[O:4].[NH2:21][C:22]1[C:27]([Cl:28])=[CH:26][C:25]([CH:29]([OH:32])[CH2:30][NH2:31])=[CH:24][C:23]=1[Cl:33].C([BH3-])#N.[Na+]>CO>[OH2:4].[NH2:21][C:22]1[C:23]([Cl:33])=[CH:24][C:25]([CH:29]([OH:32])[CH2:30][NH:31][CH:3]([CH3:5])[CH2:2][C:6]2[CH:20]=[CH:19][C:9]([O:10][C:11]3[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=3[OH:18])=[CH:8][CH:7]=2)=[CH:26][C:27]=1[Cl:28].[NH2:21][C:22]1[C:23]([Cl:33])=[CH:24][C:25]([CH:29]([OH:32])[CH2:30][NH:31][CH:3]([CH3:5])[CH2:2][C:6]2[CH:20]=[CH:19][C:9]([O:10][C:11]3[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=3[OH:18])=[CH:8][CH:7]=2)=[CH:26][C:27]=1[Cl:28]