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

HRID 1061685Notes

Reaction equation

HRID 1061685 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ead4280e49a24b079d1ba0021010ee39
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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