HCID 14830190, compound → HCID 15671504, compound

HRID 1088278Notes

Reaction equation

HRID 1088278 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26]I)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].[CH3:31][SH:32]>CN(C)C=O.O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][S:32][CH3:31])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 14830190HCID 14830190, compoundHCID 45051789Methylmercaptan sodium

Product 1

HCID 15671504HCID 15671504, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-iodomethyl-4-benzoyloxypyrrolidine (1.05 g) was dissolved in 10 ml of dimethylformamide, and a solution of 1.40 g of 15% methylmercaptan sodium salt in water was added thereto, followed by stirring at room temparature for 30 minutes under a nitrogen stream. The reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel thin layer chromatography to obtain (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-methylthiomethyl-4-benzoyloxypyrrolidine.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-45fcf406d46f4b23a7a84196c7b3e1e8
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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