Water → HCID 58921890, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH:4]([CH:8]([CH3:10])[CH3:9])[C:5]([NH2:7])=[CH2:6].N1C=CC=CC=1.C(Cl)(=O)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.O.C1C[O:33][CH2:32]C1>>[CH3:1][O:2][C:3](=[O:11])[CH:4]([CH:8]([CH3:9])[CH3:10])[C:5]([NH:7][C:32](=[O:33])[C:21]1[CH:20]=[CH:19][CH:24]=[CH:23][C:22]=1[O:25][CH3:26])=[CH2:6]Participants
Procedure
The crude 3-amino-2-isopropyl-but-3-enoic acid methyl ester of step (a) above in this method (Method B of Example 13) (5 g, 0.0318 mol) was dissolved in anhydrous THF (100 mL) and anhydrous pyridine (5.2 mL, 0.0637 mol) was added. Anisoyl chloride (4.28 mL, 0.0318 mol) was added dropwise, and the mixture was refluxed for 2 hours. After cooling, water (100 mL) was added and the organic layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with 1N HCl (3×100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The product was purified by column chromatography over silica gel (200400 mesh) eluting with 10% EtOAc/hexanes to give 2-isopropyl-3-(2-methoxy-benzoylamino)but-3-enoic acid methyl ester (3 g, 33%) as a white powder.
Workup
- temperaturethe mixture was refluxed for 2 hours
- temperatureAfter cooling
- extractionthe organic layer was extracted with ethyl acetate (3×50 mL)
- washThe combined organic extracts were washed with 1N HCl (3×100 mL), water (100 mL), and brine (100 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated on a rotary evaporator
- customThe product was purified by column chromatography over silica gel (200400 mesh)
- washeluting with 10% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-47f082140c41429ca08f04a2a8ec4f8f
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491728B2
Reaction notes
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