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

HRID 1366539ノート

反応式

HRID 1366539 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-efd6c4c1571942a4a26c01b228a9ebaa
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

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