Methyl Isocyanate → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

HRID 1088273Notes

Reaction equation

HRID 1088273 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].[CH3:25][N:26]=[C:27]=[O:28]>O1CCCC1>[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:27]([NH:26][CH3:25])=[O:28])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 15671498(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (200 mg) was dissolved in 2 ml of dry tetrahydrofuran. Methyl isocyanate (0.168 ml) was added thereto. The mixture was refluxed for 10 hours and distilled to remove the solvent. The residue was purified by silica gel chromatography to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methylaminocarbonyloxymethyl-4-acetylthiopyrrolidine.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8892ac9fecf7462a8d4eda20c134e550
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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