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

HRID 2289071Notes

Reaction equation

HRID 2289071 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.[N+](C1C=CC(COC(N=C(NC(OCC2C=CC([N+]([O-])=O)=CC=2)=O)N[C@@H:53](C)[C:54]([NH:56][CH:57]2[CH2:60]N[CH2:58]2)=O)=O)=CC=1)([O-])=O>C(#N)C.O1CCCC1>[CH:3]([N:56]([CH2:54][CH3:53])[CH:57]([CH3:58])[CH3:60])([CH3:31])[CH3:4]

Participants

5

Reactant 2

HCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 178462039HCID 178462039, 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 (585 mg) in anhydrous acetonitrile (10 ml), N,N'-carbonyldiimidazole (223 mg) was added, followed by stirring at room temperature for one hour. To the reaction mixture, N,N-diisopropylethylamine (0.57 ml) and a solution of the compound (1.26 g), which had been obtained in (2), in anhydrous tetrahydrofuran (10 ml) were added. The resulting mixture was treated in a similar manner to that described in Referential Example 16-(3), whereby the title compound (1.047 g) was obtained as an amorphous substance.

Sources & evidence

ORD record
ord-8eb4841c27cd4884a11b0ccc83a8f831
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

Loading…