Methyl iodide → HCID 69491897, compound
Reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]([C:13](=[O:29])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH2:9][CH2:10]SC)([CH3:4])([CH3:3])[CH3:2].CI>>[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]1[CH2:9][CH2:10][N:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:13]1=[O:29])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
A mixture of 0.35 g (0.81 mmol) of (S)-[1-(4-benzyloxy-phenylcarbamoyl)-3-methylsulfanyl-propyl]-carbamic acid tert-butyl ester and 8.79 g (62.0 mmol) of methyliodide is stirred at RT for 3 d. Thereafter, the methyliodide is evaporated, the intermediate sulfonium salt dissolved in 15 ml of THF and treated with 0.79 ml (0.79 ml) of lithium bis-(trimethylsilyl)amide (1 M solution in THF) at 0° C. After stirring at 0° C. for 2 h, the reaction mixture is evaporated under reduced pressure and the solid residue is directly submitted to chromatography on silica gel using a 2:1 mixture of n-hexane and ethyl acetate as the eluent. There are obtained 0.175 mg (56% of theory) of (S)-[1-(4-benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a white solid. MS: m/e=383 (M+H)+.
Workup
- customThereafter, the methyliodide is evaporated
- dissolutionthe intermediate sulfonium salt dissolved in 15 ml of THF
- additiontreated with 0.79 ml (0.79 ml) of lithium bis-(trimethylsilyl)amide (1 M solution in THF) at 0° C
- stirringAfter stirring at 0° C. for 2 h
- customthe reaction mixture is evaporated under reduced pressure
- additiona 2:1 mixture of n-hexane and ethyl acetate as the eluent
Sources & evidence
- ORD record
- ord-cba6cd70016e4087a0d125b09f30dc8d
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07235581B2
Reaction notes
Loading…