(4S)-4-mercaptopyrrolidin-2-thione → Diisopropylethylamine
Reaction equation
[Si](O[C@@H]([C@H:11]1[C:44](=O)[N:13]2[C:14]([C:33](OCOC(=O)C(C)(C)C)=O)=[C:15](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:16](C)[C@@H:12]12)C)(C(C)(C)C)(C)C.S[C@@H:47]1CNC(=S)C1>C(#N)C>[CH:44]([N:13]([CH2:12][CH3:16])[CH:14]([CH3:15])[CH3:33])([CH3:11])[CH3:47]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 1 ml of acetonitrile was dissolved 20 mg of pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-diphenylphosphoryloxy-1-methylcarbapen-2-em-3-carboxylate, 4.3 mg of (4S)-4-mercaptopyrrolidin-2-thione obtained in the above (3) and 4.1 mg of N,N-diisopropylethylamine were added thereto under nitrogen gas at -20° C., and the mixture was stirred for 2 hours while gradually elevating a temperature thereof to 0° C. The reaction mixture was poured into a 0.1M phosphate buffer (pH 7) and extracted with ethyl acetate. After the extract was washed and dried, the solvent was removed under reduced pressure. The residue was purified by thin layer chromatography (solvent; ethyl acetate:n-hexane=5:5) to obtain 7 mg of pivaloyloxymethyl (1R, 5S, 6S) -6-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-[(4R) -pyrrolidin-2-thion-4-ylthio]-1-methylcarbapen-2-em-3-carboxylate as colorless crystal.
Sources & evidence
- ORD record
- ord-e7bf8d41c89c4891a05036a20f537485
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05589592
Reaction notes
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