4-Methylmorpholine → (1RS,2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenyl-1-(1,3-thiazol-2-yl)-1-propanol

HRID 1061683노트

반응식

HRID 1061683 반응식
CN1CCOCC1.[C:8]([N:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([CH2:23][C:24](O)=[O:25])[C:13](=[O:27])[CH:12]1[CH:28]([CH3:30])[CH3:29])(=[O:10])[CH3:9].ClC(OCC(C)C)=O.Cl.[NH2:40][C@@H:41]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH:42]([C:44]1[S:45][CH:46]=[CH:47][N:48]=1)[OH:43]>O1CCCC1.CS(C)=O.O>[C:8]([N:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([CH2:23][C:24]([NH:40][C@@H:41]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:42]([C:44]2[S:45][CH:46]=[CH:47][N:48]=2)[OH:43])=[O:25])[C:13](=[O:27])[CH:12]1[CH:28]([CH3:30])[CH3:29])(=[O:10])[CH3:9]

참가 물질

8

반응물 4

HCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 22284314{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acidHCID 69748243(1RS,2S)-2-amino-3-phenyl-1-(1,3-thiazol-2-yl)-1-propanol hydrochloride

생성물 1

HCID 60073849(1RS,2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenyl-1-(1,3-thiazol-2-yl)-1-propanol

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

N-Methylmorpholine (66.4 μl) is added to a solution of {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid (162 mg, Reference compound No. 51-1) in tetrahydrofuran (2.5 ml). The mixture is cooled to −10° C., isobutyl chloroformate (65.4 μl) is added to the mixture, and the whole is stirred for 15 minutes. A mixed solution of (1RS,2S)-2-amino-3-phenyl-1-(1,3-thiazol-2-yl)-1-propanol hydrochloride (150 mg, Reference compound No. 10-2) and N-methylmorpholine (132.6 μl) in tetrahydrofuran (2.5 ml) and dimethyl sulfoxide (1 ml) is added thereto, and the whole is stirred overnight. Water is added to the reaction mixture, and the whole is extracted with ethyl acetate. The extract is washed with an aqueous sodium hydrogencarbonate solution, water and saturated brine successively and dried over magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by column chromatography to give the titled compound (162.9 mg).

후처리

  1. stirringthe whole is stirred overnight
  2. extractionthe whole is extracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium hydrogencarbonate solution, water and saturated brine successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe extract is concentrated under reduced pressure
  6. customthe resulting residue is purified by column chromatography

출처 및 근거

ORD 기록
ord-20062eec12b94237b3f5613ebb52f1fa
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960575B2

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