Pyridine → (2RS,3S)-2-Acetoxy-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-4-phenylbutanenitrile

HRID 1061695Notes

Reaction equation

HRID 1061695 reaction equation
N1C=CC=CC=1.[C:7]([N:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]([CH2:22][C:23]([NH:25][C@@H:26]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]([OH:30])[C:28]#[N:29])=[O:24])[C:12](=[O:38])[CH:11]1[CH:39]([CH3:41])[CH3:40])(=[O:9])[CH3:8].[C:42](OC(=O)C)(=[O:44])[CH3:43].CN(C1C=CC=CN=1)C>C(Cl)Cl.C(OCC)(=O)C>[C:42]([O:30][CH:27]([C@@H:26]([NH:25][C:23]([CH2:22][N:13]1[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][N:10]([C:7](=[O:9])[CH3:8])[CH:11]([CH:39]([CH3:41])[CH3:40])[C:12]1=[O:38])=[O:24])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:28]#[N:29])(=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 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

Product 1

HCID 60073844(2RS,3S)-2-Acetoxy-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-4-phenylbutanenitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (0.15 ml) is added to a solution of (2RS,3S)-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenylbutanenitrile (291 mg, Compound No. 8-1) in methylene chloride (3 ml). The mixture is cooled with ice, acetic anhydride (115 μl) and dimethylaminopyridine (catalytic amount) are added to the mixture, and the whole is stirred for six hours. Ethyl acetate is added to the reaction mixture and the whole is washed with 1 N hydrochloric acid and saturated brine successively. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (317 mg).

Workup

  1. additionare added to the mixture
  2. washthe whole is washed with 1 N hydrochloric acid and saturated brine successively
  3. concentrationThe organic layer is concentrated under reduced pressure
  4. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3c09bd090b4a4b56b4407a2a561a6b54
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

Loading…