Triphenylphosphine → Methyl 3(S)-(acetylthio)butanoate
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC([O:24][CH2:25][CH3:26])=O.O[C@H:33]([CH3:39])[CH2:34][C:35]([O:37][CH3:38])=[O:36].[S:40]1C=CC=C1CC(O)=O>C1COCC1>[C:25]([S:40][C@@H:33]([CH3:39])[CH2:34][C:35]([O:37][CH3:38])=[O:36])(=[O:24])[CH3:26]Participants
6
Conditions
- Temperature
- -23 °C
Procedure
To a -23° C. solution of PPh3 (40 mmol, 10.48 g) in THF (100 mL) was added diethyl azodicarboxylate (40 mmol, 6.28 mL) dropwise and the mixture was stirred at -23° C. for 16 hours, during which time a white precipitate was obtained. A THF (30 mL) solution of methyl 3(R)-hydroxybutanoate (20 mm, 2.36 g) and thiolacetic acid (20 mmol, 2.85 mL) was slowly added and the mixture was allowed to slowly warm to 25° C. and was stirred 16 h at 25° C. Most THF was removed in vacuo and EtOAc (10 mL) and hexanes (100 mL) were added. Insolubles were removed by filtration and the residue was purified by chromatography on silica gel to afford the title compound.
Workup
- customwas obtained
- temperatureto slowly warm to 25° C.
- stirringwas stirred 16 h at 25° C
- customMost THF was removed in vacuo and EtOAc (10 mL) and hexanes (100 mL)
- additionwere added
- customInsolubles were removed by filtration
- customthe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-c977f43e78cf451fb74273bb946cb912
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05565473
Reaction notes
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