Methyl iodide → tert-butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:21])=[O:18])[CH2:13][CH2:14]SC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI>CC(C)=O.C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:13][CH2:14][N:19]([C@@H:20]([CH3:21])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]1=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl N-[(benzyloxy)carbonyl]-l-methionyl-D-alaninate (11.9 g) in acetone (75 ml) was treated with methyl iodide (18 ml) and stirred at room temperature for 72 h. The reaction mixture was then concentrated under reduced pressure to give an orange solid which was dissolved in acetonitrile (200 ml). Dowex (OH− form) resin (19.42 g) was added and the mixture stirred for 18 h at room temperature. The mixture was filtered and the resin washed with ethyl acetate. The filtrate was evaporated under reduced pressure to afford a yellow oil which was purified by Biotage™ chromatography (eluting with cyclohexane/ethyl acetate 3:2) to give the title compound (2.92 g) as a colourless oil.
Workup
- concentrationThe reaction mixture was then concentrated under reduced pressure
- customto give an orange solid which
- stirringthe mixture stirred for 18 h at room temperature
- filtrationThe mixture was filtered
- washthe resin washed with ethyl acetate
- customThe filtrate was evaporated under reduced pressure
- customto afford a yellow oil which
- customwas purified by Biotage™ chromatography (eluting with cyclohexane/ethyl acetate 3:2)
Sources & evidence
- ORD record
- ord-378d1466b4a24130adfbe39dd7c5423d
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179835B2
Reaction notes
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