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

HRID 1061684
Notes
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Reaction equation

HRID 1061684 reaction equation
CN1CCOCC1.OC1C2N=NNC=2C=CC=1.[NH2:18][C@H:19]([CH2:27][OH:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:29]([N:32]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:35]([CH2:44][C:45](O)=[O:46])[C:34](=[O:48])[CH:33]1[CH:49]([CH3:51])[CH3:50])(=[O:31])[CH3:30].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C>[C:29]([N:32]1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:35]([CH2:44][C:45]([NH:18][C@@H:19]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:27][OH:28])=[O:46])[C:34](=[O:48])[CH:33]1[CH:49]([CH3:51])[CH3:50])(=[O:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 447213phenylalaninol, (S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22284314{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 60073846
(2S)-2-{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenyl-1-propanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methylmorpholine (525 μl), hydroxybenzotriazole (647 mg) and L-phenylalaninol (491 mg) are added to a solution of {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid (1.01 g, Reference compound No. 51-1) in methylene chloride (25 ml). The mixture is cooled with ice, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is added to the mixture, and the whole is stirred for three days. Ethyl acetate is added to the reaction mixture, and the whole is washed with a 0.1 N aqueous sodium hydroxide solution, saturated brine, 1 N hydrochloric acid and saturated brine successively. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (1.37 g).

Workup

  1. additionis added to the mixture
  2. washthe whole is washed with a 0.1 N aqueous sodium hydroxide solution, saturated brine, 1 N hydrochloric acid and saturated brine successively
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e59264f233b44fdb85860d55a8191113
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06960575B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes