HRID2407871

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8166

Dodecanoyl chloride

C12H23ClO

HCID81531

Diisopropylethylamine

C8H19N

结构：CCCCCCCCCCCCCCCCOC[C@H](CSC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OC(C)(C)C)N=[N+]=[N-]

HCID86678275

未命名化合物

PRODUCTS

生成物

结构：CCCCCCCCCCCCCCCCOC[C@H](CSC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OC(C)(C)C)NC(=O)CCCCCCCCCCC

HCID71294491

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID9942167

Palladium hydroxide

H2O2Pd

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 25 °C

PROCEDURE

实验过程

A mixture of (5R,9R)-tert-butyl 9-azido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate (1.0 eq), Pd(OH)2 (0.5 eq), dodecanoyl chloride (2.4 eq), and DIEA (4.8 eq) in EtOAc (0.01 M) was stirred under H2 (1 atm) at 25° C. overnight. The reaction was filtered and washed with DCM. The filtrate was concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% EtOAc/Hex to give (5R,9R)-tert-butyl 9-dodecanamido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate as a colorless oil.

WORKUP

后处理

filtrationThe reaction was filtered
washwashed with DCM
concentrationThe filtrate was concentrated en vaccuo
customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d5493e82c38b4490bc9c5940d231d8f9
来源数据集: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08808703B2
来源说明: uspto-grants-2014_08

反应 SMILES

[N:1]([C@H:4]([CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:5][S:6][CH2:7][C@@H:8]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:9][C:10](=[O:26])[O:11][CH2:12][CH:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N+]=[N-].[C:52](Cl)(=[O:64])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63].CCN(C(C)C)C(C)C>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:52]([NH:1][C@H:4]([CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:5][S:6][CH2:7][C@@H:8]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:9][C:10](=[O:26])[O:11][CH2:12][CH:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:64])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]