2-Thiopheneacetic acid → HCID 14041205, compound
Reaction equation
S1C=CC=C1[CH2:6][C:7](O)=[O:8].[N:10]([C@@H:13]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH3:25])[CH2:14]1)=[N+]=[N-]>>[C:7]([NH:10][C@@H:13]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:15]([CH3:25])[CH2:14]1)(=[O:8])[CH3:6]Participants
Procedure
Under a nitrogen atmosphere, 0.27 mL (280 mg, 3.7 mmol) of thiolacetic acid was added to 210 mg (0.93 mmol) of (2S,4S)-4-azido-1-t-butoxycarbonyl-2-methylpyrrolidine. The reaction mixture was stirred at room temperature for approximately four hours and concentrated with a rotary evaporator. The resulting oil was subjected to flash column chromatography using 1:1 ethyl acetate/hexane followed by ethyl acetate as eluant to obtain 190 mg of (2S,4S)-4-acetamido-1-t-butoxycarbonyl-2-methylpyrrolidine (84% yield) as a yellow oil which solidified on standing. Recrystallization of a small sample from hexanes provided a white solid, mp 108-110 degrees C. The material thus obtained was found to be identical to the material obtained by a two-step procedure that provides for the hydrogenation of (2S,4S)-4-azido-1-t-butoxycarbonyl-2-methylpyrrolidine with hydrogen and Pd/C followed by a separate acetylation step utilizing acetic anhydride.
Workup
- concentrationconcentrated with a rotary evaporator
Sources & evidence
- ORD record
- ord-27901213c0a443848d2b8e66d54d82c4
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04956475
Reaction notes
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