Ethyl Acetate → (2RS,3S)-3-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenylbutanenitrile

HRID 1061686Notes

Reaction equation

HRID 1061686 reaction equation
[C:1]([N:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]([NH:19][C@@H:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[O:22])=[O:18])[C:6](=[O:30])[CH:5]1[CH:31]([CH3:33])[CH3:32])(=[O:3])[CH3:2].S([O-])(O)=O.[Na+].C(OCC)(=O)C.[C-:45]#[N:46].[K+]>O>[C:1]([N:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:7]([CH2:16][C:17]([NH:19][C@@H:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]([OH:22])[C:45]#[N:46])=[O:18])[C:6](=[O:30])[CH:5]1[CH:31]([CH3:33])[CH3:32])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 60073845(2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropanal

Product 1

HCID 60073839(2RS,3S)-3-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenylbutanenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

(2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropanal (630 mg, Compound No. 7-1) is suspended in water (6 ml). Sodium hydrogensulfite (160 mg), water (6 ml) and ethyl acetate (18 ml) are added to the suspension, and the mixture is stirred for 30 minutes. Potassium cyanide (105 mg) is added to the mixture, and the whole is stirred for one day. Water is added to the reaction mixture, and the whole is extracted with ethyl acetate. The extract is washed with 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 (624 mg).

Workup

  1. stirringthe whole is stirred for one day
  2. extractionthe whole is extracted with ethyl acetate
  3. washThe extract is washed with water and saturated brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe extract is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bafdffb6bf8c4ba1a289982a0c46d0b6
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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