HRID215886

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID279800

Di-tert-butyl Iminodicarboxylate

C10H19NO4

结构：CCOC(=O)O[C@@H]1C=C[C@H](n2cnc3c(N[C@H](CO)Cc4ccccc4)nc(C(=O)OC)nc32)C1

HCID67022992

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](N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C3)c2n1

HCID67022924

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

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

9-((1R,4S)-4-Ethoxycarbonyloxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (Intermediate WB) (1 eq.), di-tert-butyl iminodicarboxylate (1.1 eq.), triphenylphosphane (0.15 eq.) and TEA are dissolved in THF (deoxygenated & dry).) Tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.) is added and the reaction mixture is stirred at 50° C. for 1 hour. The reaction mixture is removed in vacuo and the title compound is obtained by column chromatography.

WORKUP

后处理

customThe reaction mixture is removed in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e4c5071b981644b2b7d254bb7e15138f
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][N:11]2[C@@H:14]2[CH2:18][C@H:17](OC(OCC)=O)[CH:16]=[CH:15]2)=[C:7]([NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:6]=1)=[O:4].[NH:36]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].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:14]2[CH2:18][C@H:17]([N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH:16]=[CH:15]2)=[C:7]([NH:25][C@H:26]([CH2:34][OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:6]=1)=[O:4]