HRID2205063

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8206

Hexadecanoyl chloride

C16H31ClO

HCID81531

Diisopropylethylamine

C8H19N

结构：CCCCCCCCCCNC(=O)OC[C@H](CSC[C@H](N)C(=O)OC(C)(C)C)OC(=O)NCCCCCCCCCC

HCID86678326

未命名化合物

PRODUCTS

生成物

结构：CCCCCCCCCCCCCCCC(=O)N[C@@H](CSC[C@@H](COC(=O)NCCCCCCCCCC)OC(=O)NCCCCCCCCCC)C(=O)OC(C)(C)C

HCID86678327

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of (R)-tert-butyl 2-amino-3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)propanoate in dry DCM (0.1 M) at 0° C. was added DIEA (1.2 eq) and palmitoyl chloride (1.1 eq). The reaction was allowed to warm to room temperature then stirred for 16 hours. The crude reaction was then concentrated and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient 0-60% EtOAc/Hex to afford the title compound as a white solid.

WORKUP

后处理

customThe crude reaction
concentrationwas then concentrated
custompurified by flash chromatography on a COMBIFLASH® system (ISCO)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f61b9a51991d444ab9d1fb5f590e045d
来源数据集: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09365506B2
来源说明: uspto-grants-2016_06

反应 SMILES

[NH2:1][C@@H:2]([CH2:10][S:11][CH2:12][C@H:13]([O:29][C:30](=[O:42])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:14][O:15][C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CCN(C(C)C)C(C)C.[C:52](Cl)(=[O:68])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]>C(Cl)Cl>[CH2:32]([NH:31][C:30]([O:29][C@H:13]([CH2:14][O:15][C:16](=[O:28])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:12][S:11][CH2:10][C@H:2]([NH:1][C:52](=[O:68])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])=[O:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]