Acetic Acid → (2S,4S)-2-(2-fluoroethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 703578Notes

Reaction equation

HRID 703578 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][O:24][CH2:25][CH2:26][F:27])[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C.O>CO.C(OCC)(=O)C>[F:27][CH2:26][CH2:25][O:24][CH2:23][C@@H:7]1[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 18642555(2S,4S)-4-acetylthio-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 14884036(2S,4S)-2-(2-fluoroethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 59.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.70 g) in methanol (35 ml) was dropwise added a 28% solution (1.2 ml) of sodium methoxide in methanol at -10°~-5° C. in a nitrogen stream, followed by stirring at the same temperature for 1 hour. To the mixture was added acetic acid (0.4 ml) at -10°~-5° C. The mixture was concentrated under reduced pressure to give a residue. The residue was poured into a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (25 g) and eluted with chloroform to give (2S,4S)-2-(2-fluoroethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.91 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-3ca00c170c274e958febaaf910215ae2
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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