Diisopropyl Ether → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester
Reaction equation
CN1CC[O:5][CH2:4][CH2:3]1.ClC(O[CH2:12][CH:13]([CH3:15])[CH3:14])=O.C([CH2:23][C@H:24]([NH2:28])[C:25]([OH:27])=[O:26])C[C@@H](N)C(O)=O.NC[C:31]([OH:33])=[O:32].C[Si]([CH:38]([Si](C)(C)C)[C:39]([NH2:41])=[O:40])(C)C.C(OC(C)C)(C)C>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[NH:28]([C:31]([O:33][C:13]([CH3:12])([CH3:14])[CH3:15])=[O:32])[C@@H:24]([C:25]([O:27][N:41]1[C:4](=[O:5])[CH2:3][CH2:38][C:39]1=[O:40])=[O:26])[CH3:23]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
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-be837b3b775a4ee6b92749e12472b3a1
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539155
Reaction notes
Loading…