4-Methylmorpholine → (S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide
Reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:18][NH:19][O:20][CH3:21].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH3:18][N:19]([O:20][CH3:21])[C:14](=[O:16])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-Boc-L-leucine (2.47 g), N,O-dimethylhydroxylamine hydrochloride (1.09 g), 1-hydroxybenzotriazole monohydrate (1.51 g), and N-methylmorpholine (1.21 mL) was dissolved in DMF (40 mL), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.14 g) was added at 0° C. and the mixture was stirred at 0° C. for 2h, then at room temperature for 22 h. The reaction was quenched with water (100 mL) and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine, then dried over anhydrous MgSO4, filtered, and evaporated to afford the product (2.57 g) as an oil.
Workup
- customThe reaction was quenched with water (100 mL)
- extractionthe mixture was extracted with EtOAc (3×100 mL)
- washThe combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5a2f7bdc6da44fae9841726aae989bf5
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660268B1
Reaction notes
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