Dimethylamine, hydrochloride → L-trans4Hydroxyproline N,N-dimethylamide hydrochloride
Reaction equation
C([N:8]1[CH2:16][C@H:14]([OH:15])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])(OC(C)(C)C)=O.[CH:17]([N:20](CC)[CH:21](C)C)(C)C.[ClH:26].CNC>ClCCl.CN(C)C1C=CN=CC=1.Cl.O1CCOCC1>[CH2:13]1[C@@H:9]([C:10]([OH:12])=[O:11])[NH:8][CH2:16][C@@H:14]1[OH:15].[ClH:26].[CH3:17][N-:20][CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
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 vacua. The residue was azeotroped with toluene and diethyl ether to give a white solid; yield 0.45 g (17%).
Workup
- washwashed with 0.3M KHSO4, saturated sodium bicarbonate solution and brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customto give a colourless gum
- stirringstirred at room temperature for 1 hr
- concentrationconcentrated in vacua
- customThe residue was azeotroped with toluene and diethyl ether
- customto give a white solid
Sources & evidence
- ORD record
- ord-bb307fc894aa47c9b5892e951dbd34e2
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074781B2
Reaction notes
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