4-Methylmorpholine → (S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][O:19][NH2:20].ON1C2C=CC=C[C:25]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.CN1CCOCC1>ClCCl>[CH3:18][O:19][N:20]([CH3:25])[C:14](=[O:16])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 8.30 g (34.6 mmol) of N-(t-butyloxycarbonyl)-L-leucine, 4.03 g (41.5 mmol) of methoxyamine hydrochloride, 5.60 g (41.5 mmol) of 1-hydroxybenzotriazole, 8.55 g (41.5 mmol) of dicyclohexylcarbodiimide, and 4.56 ml (41.5 mmol) of 4-methylmorpholine in 200 ml of dichloromethane was stirred at ambient temperature for 24 h. The resulting mixture was filtered, and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and 1N HCl, and the organic phase was washed sequentially with aqueous NaHCO3 and saturated brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography using 30% ethyl acetate in hexane provided 7.16 g (76%) of the desired compound (Rf 0.21, 3:1 hexane:ethyl acetate).
Workup
- filtrationThe resulting mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was partitioned between ethyl acetate and 1N HCl
- washthe organic phase was washed sequentially with aqueous NaHCO3 and saturated brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-affe6e3709224601bcba449ff2e34693
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130468
Reaction notes
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