4-Methylmorpholine → (2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoate

HRID 58818

Reaction equation

HRID 58818 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]([OH:34])=O)[CH2:27][CH2:26]1.Cl.[NH2:36][C@@H:37]([C@H:42]([OH:44])[CH3:43])[C:38]([O:40][CH3:41])=[O:39].CN1CCOCC1>ClCCl>[OH:44][C@H:42]([CH3:43])[C@H:37]([NH:36][C:32](=[O:34])[CH2:31][N:28]1[CH2:27][CH2:26][O:25][CH2:30][CH2:29]1)[C:38]([O:40][CH3:41])=[O:39]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 4389684-Morpholineacetic acidHCID 2734893Methyl L-threoninate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 117608206(2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoateYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (7.66 g, 20.1 mmol) was added to a solution of 2-morpholinoacetic acid (2.44 g, 16.8 mmol) and (2S,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (2.84 g, 16.8 mmol) in dichloromethane (20 mL) at 0° C. N-Methylmorpholine (5.1 g, 50.4 mmol) was added and the reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. The mixture was concentrated and the residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=100:1 to 60:1) to afford (2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoate (2.1 g, 48% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=100:1 to 60:1)

Sources & evidence

ORD record
ord-1d62453ce0004896ace76155e6286cbf
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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