Water → HCID 178473748, compound

HRID 1061696Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].C(OC([C@@H](N[C:25]([CH2:27][N:28]1[C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:32][N:31]([C:40](=O)[CH3:41])[CH:30]([CH:43]([CH3:45])[CH3:44])[C:29]1=[O:46])=O)CC1C=CC=CC=1)C#N)(=O)C.[OH2:47]>O1CCCC1>[C:40]([N:31]1[CH:32]=[C:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:28]([C@@H:27]([CH2:25][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]([C:30]2[NH:31][N:3]=[N:2][N:1]=2)[OH:46])[C:29](=[O:46])[CH:30]1[CH:43]([CH3:45])[CH3:44])(=[O:47])[CH3:41]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium azide (75.3 mg) and aluminum chloride (386 mg) are added to a solution of (2RS,3S)-2-acetoxy-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-4-phenylbutanenitrile (299 mg, Compound No. 18-1) in tetrahydrofuran (3.5 ml), and the mixture is stirred for two hours. The reaction mixture is warmed to 60° C. and stirred for three hours. The reaction mixture is cooled to room temperature, then water is added to the reaction mixture, and the whole is extracted with ethyl acetate. 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 (242 mg).

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionthe whole is extracted with ethyl acetate
washThe extract is washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationThe extract is concentrated under reduced pressure
customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c8aa1168fb8f41f78427b08467f8e8f5
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960575B2

Reaction notes

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