Tetrahydrofuran → Diisopropylethylamine

HRID 2289076Notes

Reaction equation

HRID 2289076 reaction equation
COC1C=CC(CS[C@@H:9]2[CH2:13][N:12](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H:11]([C:27](O)=O)[CH2:10]2)=CC=1.O1[CH2:36][CH2:35][CH2:34]C1>C(#N)C>[CH:35]([N:12]([CH2:13][CH3:9])[CH:11]([CH3:27])[CH3:10])([CH3:36])[CH3:34]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 15297071(2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,4S)-4-(4-methoxybenzyl)thio-1-(4-nitrobenzyloxycarbonyl)-L-proline (1.28 g) in anhydrous acetonitrile (19 ml), N,N'-carbonyldiimidazole (489 mg) was added, followed by stirring at room temperature for one hour. To the reaction mixture, N,N-diisopropylethylamine (478 μl) and a solution of the compound (2.60 g), which had been obtained in (1), 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 (2.09 g) was obtained as an amorphous substance.

Sources & evidence

ORD record
ord-2207fbdcd7cf4108aa3731f858f8b6a2
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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