Sodium hydride → HCID 60073855, compound

HRID 1061692Notes

Reaction equation

HRID 1061692 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:10][C:8](=[O:9])[NH:7][C:5]1=[O:6].[C:11]([N:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([CH2:26][C:27]([NH:29][C@@H:30]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:31](OC2C=CC([N+]([O-])=O)=CC=2)=[O:32])=[O:28])[C:16](=[O:50])[CH:15]1[CH:51]([CH3:53])[CH3:52])(=[O:13])[CH3:12].[Cl-].[NH4+]>O1CCCC1>[C:11]([N:14]1[CH:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:17]([CH2:26][C:27]([NH:29][C@@H:30]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:31]([N:7]2[C:8](=[O:9])[CH2:10][N:4]([CH3:3])[C:5]2=[O:6])=[O:32])=[O:28])[C:16](=[O:50])[CH:15]1[CH:51]([CH3:53])[CH3:52])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 692171-MethylhydantoinHCID 60073852HCID 60073852, compound

Product 1

HCID 60073855HCID 60073855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride (200 mg) is added to a solution of 1-methylhydantoin (571 mg) in anhydrous tetrahydrofuran (20 ml), and the mixture is stirred for 20 minutes. Then, 4-nitrophenyl (2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropionate (1.17 g, Compound No. 14-1) is added to the mixture, and the whole is stirred for three days. A saturated aqueous ammonium chloride solution is added to the reaction mixture, and the whole is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium hydrogencarbonate solution 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 (116 mg).

Workup

  1. addition14-1) is added to the mixture
  2. stirringthe whole is stirred for three days
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe extract is washed with a saturated aqueous sodium hydrogencarbonate solution 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-e49de5de7d8f43fdb0f6ecc426f994f9
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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