Dimethylamine, hydrochloride → L-trans4Hydroxyproline N,N-dimethylamide hydrochloride

To a solution of BOC-hydroxyproline (2.99 g, 13.89 mmol) in dichloromethane (100 ml) were added N,N-diisopropylethylamine (3.7 ml, 21.24 mmol), 4-(dimethylamino)pyridine (1.74 g, 14.24 mmol), dimethylamine hydrochloride (1.72 g, 21.09 mmol) and WSCDI (3.17 g, 16.68 mmol). The mixture was stirred at room temperature for 30 hr. The mixture was diluted with dichloromethane (100 ml) and washed with 0.3M KHSO4, saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated in vacuo to give a colourless gum. This crude material was taken up in 4N HCl/dioxan (50 ml) and stirred at room temperature for 1 hr and then concentrated in vacuo. The residue was azeotroped with toluene and diethyl ether to give a white solid; yield 0.45 g (17%).

1. washwashed with 0.3M KHSO4, saturated sodium bicarbonate solution and brine
2. dry with materialdried over MgSO4
3. concentrationconcentrated in vacuo
4. customto give a colourless gum
5. stirringstirred at room temperature for 1 hr
6. concentrationconcentrated in vacuo
7. customThe residue was azeotroped with toluene and diethyl ether
8. customto give a white solid

ORDレコード

ord-da9920f0bdc9413dba4c294c5971ecc5

出典データセット

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07560454B2