HRID25729

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COC(=O)NCCCCCCC(CCCC(=O)NCCCN[C@H](C(=O)OC(C)(C)C)[C@@H](O)C1O[C@@H](n2ccc(=O)n(Cc3ccc(OC)cc3)c2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)C1c2ccccc2-c2ccccc21

HCID86587946

未命名化合物

PRODUCTS

生成物

结构：COc1ccc(Cn2c(=O)ccn([C@@H]3OC([C@H](O)[C@H](NCCCNC(=O)CCCCCCCCCCN)C(=O)OC(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)c2=O)cc1

HCID10191481

未命名化合物

收率 51%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8082

Piperidine

C5H11N

PROCEDURE

实验过程

By using an analogous procedure to that described for Reference Example 32, a solution of tert-butyl (21S)-21-[(R)-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-11-(9H-fluoren-9-yl)-3,15-dioxo-2-oxa-4,16,20-triazadocosan-22-oate (106 mg, 0.09 mmol, obtained from Example 24) in piperidine (3 ml) was stirred for 1.5 hours under nitrogen at room temperature. The product was purified by chromatography (flash column, silica gel, 60-100% methanol in methylene chloride) to provide tert-butyl (2S,3R)-2-({3-[(11-aminoundecanoyl)amino]propyl}amino)-3-[(3R,4R,5R)-3,4-bis{[tert-butyl (dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate (44 mg, 51%) as a white solid.

WORKUP

后处理

customThe product was purified by chromatography (flash column, silica gel, 60-100% methanol in methylene chloride)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c8a3f1707a11479f90cdd6a6fe8a1695
来源数据集: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06858591B2
来源说明: uspto-grants-2005_02

反应 SMILES

[Si:1]([O:8][C@H:9]1[C@@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:23]2=[O:38])[O:11][CH:10]1[C@H:39]([OH:83])[C@@H:40]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[NH:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:75])[CH2:47][CH2:48][CH2:49][CH:50](C1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][NH:57]C(=O)OC)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>N1CCCCC1>[NH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][C:46]([NH:45][CH2:44][CH2:43][CH2:42][NH:41][C@@H:40]([C@H:39]([CH:10]1[C@@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])[C@@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:23]2=[O:38])[O:11]1)[OH:83])[C:76]([O:78][C:79]([CH3:80])([CH3:81])[CH3:82])=[O:77])=[O:75]