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

HRID 227225

Reaction equation

HRID 227225 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

7

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 131725849L-trans4Hydroxyproline N,N-dimethylamide hydrochloride

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 204431481,4-Dioxane hydrochlorideSolvent

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 vacuo. The residue was azeotroped with toluene and diethyl ether to give a white solid; yield 0.45 g (17%).

Workup

  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

Sources & evidence

ORD record
ord-da9920f0bdc9413dba4c294c5971ecc5
Source dataset
uspto-grants-2009_07
Patent number
US07560454B2

Linked notes

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