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

HRID 1061694Notes

Reaction equation

HRID 1061694 reaction equation
CON(C)[C:4](=[O:36])[C@@H:5]([NH:13][C:14]([CH2:16][N:17]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][N:20]([C:29](=[O:31])[CH3:30])[CH:19]([CH:32]([CH3:34])[CH3:33])[C:18]1=[O:35])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Li].O1CCC[CH2:41]1.C1(C(C)C)C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[C:29]([N:20]1[CH:21]=[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:17]([CH2:16][C:14]([NH:13][C@@H:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:36])[CH3:41])=[O:15])[C:18](=[O:35])[CH:19]1[CH:32]([CH3:34])[CH3:33])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86592307N1-methoxy-N1-methyl-(2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropionamideHCID 178420641HCID 178420641, compound

Product 1

HCID 60073842(3S)-3-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-oxo-4-phenylbutane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N1-methoxy-N1-methyl-(2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropionamide (122 mg, Compound No. 1-51) in anhydrous tetrahydrofuran (2 ml) is cooled to −78° C., a 1.0 M methyllithium/tetrahydrofuran/cumene solution (1.2 ml) is added thereto, and the mixture is stirred for 15 minutes. A saturated aqueous ammonium chloride solution is added to the reaction mixture, and the temperature is raised to 0° C. The whole is extracted with ethyl acetate, and the extract is washed with saturated brine 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 (53.8 mg).

Workup

  1. extractionThe whole is extracted with ethyl acetate
  2. washthe extract is washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe extract is concentrated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-739327cf433f4f8ab98cbd059bd8ae2a
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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