Tetrahydrofuran → HCID 70050348, compound
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5](C(OC)=O)=[CH:4][CH:3]=1.Cl[C:13]([O:16][C:17](Cl)=[O:18])(Cl)Cl.[CH2:20]([O:27][C:28](=[O:34])[C@H:29]([CH:31]([CH3:33])[CH3:32])[NH2:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.[O:42]1CCC[CH2:43]1>>[CH2:20]([O:27][C:28](=[O:34])[C@H:29]([CH:31]([CH2:32][C:17]([O:16][CH3:13])=[O:18])[CH3:33])[NH:30][C:43]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:10][CH:11]=1)=[O:42])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Procedure
To a solution of methyl p-aminobenzoate (0.4 g) in tetrahydrofuran (10 ml) was added trichloromethylchloroformate (0.31 g) and the mixture was allowed to stand overnight at room temperature. L-Valine benzyl ester (0.54 g) was added to the solution and the pH of the mixture was neutralized with triethylamine. After being stirred for 30 minutes at room temperature, the mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate (10 ml). The extract was washed with 1N-hydrochloric acid (10 ml) and aqueous sodium bicarbonate (10 ml) and concentrated to dryness to give 4-(methoxycarbonyl)phenylaminocarbonyl-L-valine benzyl ester (1.17 g).
Workup
- concentrationthe mixture was concentrated under reduced pressure
- extractionthe residue was extracted with ethyl acetate (10 ml)
- washThe extract was washed with 1N-hydrochloric acid (10 ml) and aqueous sodium bicarbonate (10 ml)
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-21a4b567e015463798eac326e568c36d
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05296591
Reaction notes
Loading…