Reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH2:13][C:14]([OH:16])=O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH:30]1[CH2:36][CH2:35][CH2:34][C@H:31]1[CH2:32][OH:33]>C1COCC1.C(OCC)(=O)C.O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH2:13][C:14]([N:30]2[CH2:36][CH2:35][CH2:34][C@H:31]2[CH2:32][OH:33])=[O:16])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
3-[N-(2-phenylethyl)carbamoyl]propionic acid (400 mg) was dissolved into dry THF (4 ml). Triethylamine (0.32 ml) and ethyl chloroformate (0.15 ml) secondary were dropped into the solution with stirring at 0° C. After 10 mins' stirring, a solution of L-prolinol (199 mg) in THF (2 ml) was added to the solution, and the solution was stirred for 30 mins at 0° C. and for another 30 mins at room temperature. Water was added to the diluted solution with ethyl acetate. The oily layer was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrocarbonate, a saturated brine, successively, dried and then evaporated. The residue was purified by column chromatography on silica gel to give the title compound (490 mg).
Workup
- stirringAfter 10 mins' stirring
- stirringthe solution was stirred for 30 mins at 0° C. and for another 30 mins at room temperature
- washThe oily layer was washed with 1N hydrochloric acid
- dry with materiala saturated aqueous solution of sodium hydrocarbonate, a saturated brine, successively, dried
- customevaporated
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-cb32c3a300b4415dbbd0beee7480c91a
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05254550
Linked notes
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