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

HRID 1061685ノート

反応式

HRID 1061685 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ead4280e49a24b079d1ba0021010ee39
出典データセット
uspto-grants-2005_11
特許番号
US06960575B2

反応ノート

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