HRID2384905

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID13831

Tributylphosphine

C12H27P

HCID75555

未命名化合物

结构：COc1cc(NC(=O)c2sc(-c3ccc(Cl)cc3)cc2CCO)ccc1OC1CN(C(=O)OC(C)(C)C)C1

HCID68952325

未命名化合物

PRODUCTS

生成物

结构：COc1cc(N2CCc3cc(-c4ccc(Cl)cc4)sc3C2=O)ccc1OC1CN(C(=O)OC(C)(C)C)C1

HCID68949177

未命名化合物

收率 67.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Dissolve 3-(4-{[5-(4-chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (840 mg, 1.50 mmol) and tri-n-butylphosphine (2.25 mmol, 562 μL) in tetrahydrofuran (15 mL) and add slowly dropwise diisopropyl azodicarboxylate (2.25 mmol, 447 μL). Stir the mixture overnight and concentrate in vacuo. Triturate the residue with Et2O, filter, and dry in vacuo to afford 550 mg (62%) of the title compound as a white solid. LC-MS/ES m/z (35Cl) 441.0 [M-tBuCO2+H]+.

WORKUP

后处理

concentrationconcentrate in vacuo
customTriturate the residue with Et2O
filtrationfilter
customdry in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3217c36b1167486e9c194166e7e54bcc
来源数据集: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08263772B2
来源说明: uspto-grants-2012_09

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[S:23][C:24]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[CH:25][C:26]=3[CH2:27][CH2:28]O)=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(CCCC)CCCC)CCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:28][CH2:27][C:26]4[CH:25]=[C:24]([C:30]5[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=5)[S:23][C:22]=4[C:20]3=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]