Sodium Carbonate → Methyl (3R)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate

HRID 1451871Notes

Reaction equation

HRID 1451871 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]12

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 461664Methyl 3-phthalimido-3-(3,4-dimethoxyphenyl)propionateHCID 7131801(R)-methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate

Product 1

HCID 9842256Methyl (3R)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate

Procedure

Prepared as described earlier as methyl 3-phthalimido-3-(3',4'-dimethoxyphenyl)propionate from methyl (3R)-3-amino-3-(3',4'-dimethoxyphenyl)propionate (0.25 g, 0.91 mmol), sodium carbonate (0.10 g, 0.91 mmol) and N-carboethoxyphthalimide (0.20 g, 0.91 mmol). Methyl (3R)-3-phthalimido-3-(3',4'-dimethoxyphenyl)propionate was obtained as a white powder, 0.29 g (88%); 1H NMR (DMSO-d6, 250 MHz) δ 7.87 (br s, 4 H, Ar), 6.80-7.10 (m, 3 H, Ar), 5.64 (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, 167.6, 148.6, 148.4, 134.7, 131.1, 131.0, 123.2, 119.2, 111.7, 111.0, 55.5, 51.6, 49.9, 35.6. Anal. Calcd for C20H19NO6 @0.80 H2O. Theoretical C, 62.60; H, 4.99; N, 3.69. Found C, 62.60; H, 4.93; N, 3.69. HPLC 99.9%.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0c22ae17d42c4dd0859c9d49cfc51857
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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