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

HRID 1061685노트

반응식

HRID 1061685 반응식
C(N(CC)CC)C.[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:26][C@@H:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:28][OH:29])=[O:25])[C:13](=[O:37])[CH:12]1[CH:38]([CH3:40])[CH3:39])(=[O:10])[CH3:9].O>CS(C)=O>[C:8]([N:11]1[CH:16]=[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:14]([CH2:23][C:24]([NH:26][C@@H:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[O:29])=[O:25])[C:13](=[O:37])[CH:12]1[CH:38]([CH3:40])[CH3:39])(=[O:10])[CH3:9]

참가 물질

5

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 60073846(2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenyl-1-propanol

생성물 1

HCID 60073845(2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropanal수율 46.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Triethylamine (2.60 ml) is added to a solution of (2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenyl-1-propanol (1.37 g, Compound No. 6-1) in dimethyl sulfoxide (16 ml). A sulfur trioxide-pyridine complex (1.7 g) is added to the mixture, and the whole is stirred overnight. Water is added to the reaction mixture, and the whole is stirred for one hour and extracted with ethyl acetate. The extract is washed with a saturated aqueous ammonium chloride solution, water and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (631 mg).

후처리

  1. additionA sulfur trioxide-pyridine complex (1.7 g) is added to the mixture
  2. stirringthe whole is stirred for one hour
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with a saturated aqueous ammonium chloride solution, water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ead4280e49a24b079d1ba0021010ee39
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960575B2

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