Trichloroacetyl isocyanate → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

HRID 1088266Notes

Reaction equation

HRID 1088266 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][OH:22])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:25][C:26]([Cl:33])([Cl:32])[C:27]([N:29]=[C:30]=[O:31])=[O:28]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][O:22][C:30]([NH:29][C:27](=[O:28])[C:26]([Cl:33])([Cl:32])[Cl:25])=[O:31])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 15671474(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (100 mg) was dissolved in 3 ml of dry ethyl acetate. To the solution was added 0.05 ml of trichloroacetyl isocyanate under ice-cooling in a nitrogen stream, followed by stirring at the same temperature for 1 hour. The mixture was diluted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine.

Workup

  1. temperaturecooling in a nitrogen stream
  2. washwashed successively with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled

Sources & evidence

ORD record
ord-8f29ef83300346bba7a80ab2a8e51b54
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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