1,1'-Carbonyldiimidazole → Diisopropylethylamine
Reaction equation
CO[C:3]1[CH:31]=CC(CS[C@@H]2CN(C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H](C(O)=O)C2)=C[CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[N+](C1C=CC(COC(N=C(NC(OCC2C=CC([N+]([O-])=O)=CC=2)=O)N[CH2:65][C:66]([NH:68][CH:69]2[CH2:72]N[CH2:70]2)=O)=O)=CC=1)([O-])=O>C(#N)C>[CH:3]([N:68]([CH2:66][CH3:65])[CH:69]([CH3:70])[CH3:72])([CH3:31])[CH3:4]Participants
Procedure
To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (1.43 g) in anhydrous acetonitrile (22 ml), N,N-carbonyldiimidazole (545 mg) was added. The resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture, N,N-diisopropylethylamine (581 μl) and a solution of the compound (2.78 g), which had been obtained in (2), in anhydrous acetonitrile (23 ml) were added and the mixture was stirred overnight at room temperature. To the reaction mixture, dichloromethane was added. The resulting mixture was washed with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure, whereby 2.57 g of the title compound were obtained as a colorless amorphous substance.
Sources & evidence
- ORD record
- ord-3e5b74a0250a45798417a6afc8e48f86
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090802
Reaction notes
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