Sodium Carbonate → Methyl (S)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate
Reaction equation
[C:1]1(=[O:27])[N:5]([CH:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:22])[C:3]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:2]12.N[C@H](C1C=CC(OC)=C(OC)C=1)CC(OC)=O.C(=O)([O-])[O-].[Na+].[Na+].C(N1C(=O)C2=CC=CC=C2C1=O)(OCC)=O>>[C:4]1(=[O:22])[N:5]([C@H:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:1](=[O:27])[C:2]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:3]12Participants
Procedure
Prepared as described earlier as methyl 3-phthalimido-3-(3',4'-dimethoxyphenyl)propionate from methyl (S)-3-amino-3-(3',4'-dimethoxyphenyl)propionate (0.45 g, 1.63 mmol), sodium carbonate (0.17 g, 1.63 mmol) and N-carboethoxyphthalimide (0.36 g, 1.63 mmol). methyl (S)-3-phthalimido-3-(3',4'-dimethoxyphenyl)propionate was obtained as a white powder, 0.51 g (85%); 1H NMR (DMSO-d6, 250 MHz) δ 7.87 (br s, 4 H, Ar), 6.80-7.10 (m, 3 H, Ar), 5.65 (dd, 1 H, J1 =7 Hz, J2 =9 Hz), 3.73 (s, 3 H, OCH3), 3.72 (s, 3 H, OCH3), 3.55 (s, 3 H, OCH3), 3.30-3.67 (m, 2 H) ; 13C NMR (DMSO-d6) δ 170.8, 167.7, 148.6, 148.4, 134.7, 131.1, 131.0, 123.2, 119.3, 111.7, 111.0, 55.5, 51.6, 49.9, 35.6. Anal. Calcd for C20H19NO6. Theoretical C, 65.03; H, 5.18; N, 3.79. Found C, 64.94; H, 5.29; N, 3.86. HPLC 97%.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-ef9af8d1625f4aad9177f194041f85fe
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05605914
Reaction notes
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