(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline → Diisopropylethylamine

HRID 2289073Notes

Reaction equation

HRID 2289073 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.FC(F)(F)C(O)=O.CN([CH2:70][C:71]([NH:73][C@H:74]1[CH2:78]CN[CH2:75]1)=O)C(NC(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=NC(OCC1C=CC([N+]([O-])=O)=CC=1)=O>C(#N)C.O1CCCC1>[CH:3]([N:73]([CH2:71][CH3:70])[CH:74]([CH3:75])[CH3:78])([CH3:31])[CH3:4]

Participants

5

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 86755555HCID 86755555, compound

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (1.05 g) in anhydrous acetonitrile (10 ml), N,N'-carbonyldiimidazole (401 mg) was added, followed by stirring at room temperature. To the reaction mixture, N,N-diisopropylethylamine (392 μl) and a solution of the compound (2.02 g), which had been obtained in (2), in anhydrous tetrahydrofuran (15 ml) were added. The resulting mixture was treated in a similar manner to that described in Referential Example 16-(3), whereby the title compound (1.69 g) was obtained as an amorphous substance.

Sources & evidence

ORD record
ord-26011dca025749c581582ccce5d0f61e
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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