4-Methylmorpholine → Morpholine-4-carboxamide

HRID 439628

반응식

HRID 439628 반응식
N[C@@H]([C:10]([OH:12])=O)CC1C=CC=CC=1.C[N:14]1CCOCC1.C(OC(Cl)=O)C(C)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C1COCC1.CCOCC>[N:28]1([C:10]([NH2:14])=[O:12])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 62365Isobutyl chloroformateHCID 71567D-Phenylalanine

생성물 1

HCID 75088Morpholine-4-carboxamide수율 94%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 100 mg (0.296 mmol) of carboxylic acid derived from D-phenylalanine in 10 mL of THF at -8° C. was treated with 39.0 mg (0.385 mmol) of N-methylmorpholine followed by 54.7 mg (0.400 mmol) of isobutylchloroformate. After stirring for 5 min 34.8 mg (0.400 mmol) of morpholine was added and the reaction mixture allowed to warm to room temperature. After 15 min at room temperature, 50 mL of Et2O was added and the mixture dried over MgSO4, filtered, and concentrated under reduced pressure to afford a residue which was chromatographed (silica, gradient elution 30→100% : EtOAc/hexanes) to provide 112.8 mg (94% yield) of the morpholino amide derived from D-phenylalanine: a!D24 -95° (C 0.85, CHCl3); IR (CHCl3) 3495 (w), 3000 (s), 2980 (w), 1745 (m), 1700 (s), 1635 (m), 1495 (s), 1445 (m), 1230 (m), 1165 (m), 1115 (m), 1075 (w), 1045 (m), 1025 (w) cm-1 ; 1H NMR (500 MHz, CDCl3) d 7.27-7.22 (m, 3H), 7.04-7.02 (m, 2H), 5.71 (s, 1H), 3.91 (d, J=15.3 Hz, 1H), 3.75 (s, 3H), 3.69-3.57 (m, 7H), 3.50-3.46 (m, 2H), 3.01 (d, J=13.3 Hz, 1H), 2.91 (d, J=15.5 Hz, 1H), 1.46 (s, 9H); 13C NMR (62.5 MHz, CDCl3) d 172.37, 168.08, 154.19, 135.20, 129.57 (2C), 127.97 (2C), 126.88, 79.18, 66.68, 66.54, 62.44, 52.41, 46.11, 41.81, 40.92, 38.12, 28.20 (3C); high resolution mass spectrum (CI, methane) m/z 407.2123 (M+H)+ ; calculated for C21H31N2O6 : 407.2182!.

후처리

  1. additionwas added
  2. dry with materialthe mixture dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford a residue which
  6. customwas chromatographed
  7. wash(silica, gradient elution 30→100% : EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-4556ffa382cf4278959987178380c77b
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514814

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