1,2-Dichloroethane → (3S)-N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide

HRID 1366539Notes

Reaction equation

HRID 1366539 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:6]([C:15]([OH:17])=O)[CH2:5][O:4][CH2:3]1.[CH3:18][NH:19][CH3:20].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>C1COCC1>[CH3:18][N:19]([CH3:20])[C:15]([C@@H:6]1[CH2:5][O:4][CH2:3][C:2](=[O:1])[N:7]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

Product 1

HCID 66936283(3S)-N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (1.5 g, 6.4 mmol) (J. Chem. Soc., Perkin Trans. 1, 1985, 2577-2580) in THF (50 mL) was added dimethylamine (3.8 mL, 7.6 mmol, 2M in THF), EDC (1.46 g, 7.7 mmol), HOAt (1.06 g, 7.7 mmol) and NMM (3.5 mL, 30 mmol). The reaction mixture was stirred overnight and the THF was evaporated, replacing it with EtOAc. 1 M HCl was added and the phases were separated. The aqueous layer was extracted twice with EtOAc and the combined organics were dried over sodium sulfate. Concentration in vacuo yielded (3S)—N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide, which was purified by RP-HPLC. LCMS: (M+H)+: 263.1.

Workup

  1. customthe THF was evaporated
  2. addition1 M HCl was added
  3. customthe phases were separated
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. dry with materialthe combined organics were dried over sodium sulfate
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-efd6c4c1571942a4a26c01b228a9ebaa
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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