Reaction equation
CI.[CH2:3]([O:10][C:11](=[O:26])[CH2:12][CH2:13][C@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15]([OH:17])=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:27]([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.C(Cl)(Cl)Cl.CO>[C:22]([O:21][C:19]([NH:18][C@@H:14]([CH2:13][CH2:12][C:11]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:26])[C:15]([O:17][CH3:27])=[O:16])=[O:20])([CH3:23])([CH3:25])[CH3:24]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl iodide (1.01 mL, 16.3 mmol) was added dropwise to a solution of (2S)-5-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid XII (5.00 g, 14.82 mmol) and K2CO3 (2.25 g, 16.3 mmol) in DMF (25 mL) at room temperature The reaction mixture was stirred about 3 h at room temperature before adding additional methyl iodide (1.01 mL, 16.3 mmol). EtOAc was then added to the reaction and washed 3×10% Na2S2O3 and dried over MgSO4. The solvent was removed under reduced pressure and the crude product was purified on a silica gel column (100:1 and then 50:1 CHCl3/MeOH) to give 5-benzyl 1-methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}pentanedioate XIII (4.20 g, 12.23 mmol, 82% yield). ESIMS found for C18H25NO6 m/z 352 (M+H).
Workup
- washwashed 3×10% Na2S2O3
- dry with materialdried over MgSO4
- customThe solvent was removed under reduced pressure
- customthe crude product was purified on a silica gel column (100:1
Sources & evidence
- ORD record
- ord-4fb6be60d519414a89aa4ae48a36e745
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933018B2
Linked notes
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