HRID215884

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID24758

Sodium hydride

HNa

HCID15407440

未命名化合物

结构：COC(=O)c1nc(N[C@H](CO)Cc2ccccc2)c2nc[nH]c2n1

HCID178499116

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1nc(N[C@H](CO)Cc2ccccc2)c2ncn([C@H]3C=C[C@@H](O)C3)c2n1

HCID67022956

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

6-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (1.05 eq.) is suspended in THF (deoxygenated & dry). NaH (1.05 eq.) is added over 5 minutes and the reaction mixture is stirred at RT over 30 minutes. A solution of acetic acid (1S,3R)-3-hydroxy-cyclopentyl ester (1 eq.), triphenylphosphane (0.15 eq.) and tris(dibenzylideneacetone)dipalladium(0) in THF (deoxygenated & dry) is added to reaction. The reaction mixture is reflux for 6 hours. The reaction mixture is reduce in vacuo and columned to give the title compound.

WORKUP

后处理

temperatureThe reaction mixture is reflux for 6 hours

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-56c23c62e5ae44b58fae5832e3689b08
来源数据集: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08193164B2
来源说明: uspto-grants-2012_06

反应 SMILES

[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][NH:11]2)=[C:7]([NH:14][C@H:15]([CH2:23][OH:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]=1)=[O:4].[H-].[Na+].[OH:27][C@@H:28]1[CH2:32][CH2:31][C@H:30](OC(=O)C)[CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:31]2[CH2:32][C@H:28]([OH:27])[CH:29]=[CH:30]2)=[C:7]([NH:14][C@H:15]([CH2:23][OH:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]=1)=[O:4]