Dimethylformamide → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester
Reaction equation
CN1[CH2:7][CH2:6][O:5]CC1.ClC(O[CH2:12][CH:13]([CH3:15])[CH3:14])=O.C([O:29][C:30](=[O:42])[CH2:31][CH2:32]CCCCCCCCC)(=O)CCCCCCCCCCC.C[Si]([CH:47]([Si](C)(C)C)[C:48]([NH2:50])=[O:49])(C)C.C([O:58]C(C)C)(C)C.C[N:63](C)[CH:64]=[O:65]>C(Cl)Cl.C(OCC)(=O)C>[CH3:32][C@@H:31]([NH:63][C:64]([O:65][C:13]([CH3:15])([CH3:14])[CH3:12])=[O:58])[C:30]([O:29][N:50]1[C:6](=[O:5])[CH2:7][CH2:47][C:48]1=[O:49])=[O:42]Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cooled mixture of Compound (1) (2.43 g.) and N-methylmorpholine (0.71 g.) in methylene chloride (40 ml.) was added dropwise isobutyl chloroformate (960 mg.) and the mixture was stirred for 20 minutes at 0° C. To this mixture was added a solution of Compound (2) (2.83 g.) in a mixture of methylene chloride (20 ml.) and dimethylformamide (10 ml.) containing bis(trimethylsilyl)acetamide (2 ml.). The reaction mixture was stirred for 2 hours and then concentrated to give an oily residue, which was dissolved in ethyl acetate, washed with water and dried over magnesium sulfate. Evaporation of the solvent gave a white foam, which was pulverized with isopropyl ether to give Compound (3) (4.20 g.) as white powder.
Workup
- stirringThe reaction mixture was stirred for 2 hours
- concentrationconcentrated
- customto give an oily residue, which
- washwashed with water
- dry with materialdried over magnesium sulfate
- customEvaporation of the solvent
- customgave a white foam, which
Sources & evidence
- ORD record
- ord-106136a2b6c54388b448ea2cf0b1d062
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04749691
Reaction notes
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