Triacetoxyperiodinane → N-Cyclopropyl-4-methyl-3-[3-[[(1R,2R)-2-methyl-3-oxo-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([NH:26][C:27](=[O:54])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C@@H:42]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@@H:43]([CH3:46])[CH2:44][OH:45])[C:36]3=[O:53])[CH:29]=2)[CH2:25][CH2:24]1>ClCCl>[CH:23]1([NH:26][C:27](=[O:54])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C@@H:42]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@@H:43]([CH3:46])[CH:44]=[O:45])[C:36]3=[O:53])[CH:29]=2)[CH2:24][CH2:25]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of Dess-Martin periodinane (600 mg) in dichloromethane (3 mL) was added dropwise to a solution of N-cyclopropyl-3-(3-((1R,2R)-3-hydroxy-2-methyl-1-phenylpropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide (Example 136, 405 mg) in dichloromethane (4 mL) at 25° C. The resulting mixture was stirred at 25° C. for 30 minutes. The reaction mixture was quenched with sat. aqueous Na2S2O3 (7 mL) and sat. aqueous NaHCO3. The mixture was stirred for 15 min. and extracted into dichloromethane. The organic phase was dried (Na2SO4), filtered and evaporated to afford crude product (475 mg) that was used in the next step without purification.
Workup
- customThe reaction mixture was quenched with sat. aqueous Na2S2O3 (7 mL) and sat. aqueous NaHCO3
- stirringThe mixture was stirred for 15 min.
- extractionextracted into dichloromethane
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-4f02286743dd40e99cc404e3f9dadd58
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299246B2
Reaction notes
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