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

HRID 1366539노트

반응식

HRID 1366539 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-efd6c4c1571942a4a26c01b228a9ebaa
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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