Reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.Cl.[CH2:11]([C@H:13]([NH2:19])[CH2:14][O:15][N+:16]([O-:18])=[O:17])[CH3:12].C(OP(C#N)(=O)OCC)C.C(OC(C)C)(C)C>O1CCCC1.CC(C)=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:11]([C@H:13]([NH:19][C:7]([C@@H:5]1[CH2:4][S:3][C:2](=[O:1])[NH:6]1)=[O:9])[CH2:14][O:15][N+:16]([O-:18])=[O:17])[CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
In 10 ml of dry tetrahydrofuran were suspended 0.50 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 0.70 g of (1S)-1-ethyl-2-nitroxyethylamine hydrochloride, 1.40 ml of triethylamine and 0.62 ml of diethylcyanophosphoric acid were added thereto, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (1:2) as an eluent to obtain a pale yellow oil. Isopropyl ether was added to the oil to obtain a pale yellow powder. The powder was dissolved in 10 ml of acetone and further 5 ml of ethyl acetate was added thereto. The acetone was distilled off under reduced pressure and the mixture was left to stand at room temperature to obtain 0.24 g of the desired compound as colorless columnar crystals.
Workup
- additionwere added
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography
- customto obtain a pale yellow oil
- customto obtain a pale yellow powder
- distillationThe acetone was distilled off under reduced pressure
- waitthe mixture was left
- customto stand at room temperature
Sources & evidence
- ORD record
- ord-ddd5ab6763424b1c897aff453434508b
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05925658
Linked notes
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