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

HRID 1421318Notes

Reaction equation

HRID 1421318 reaction equation
[NH2:1][C@H:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])(OCC)=O>>[C:30]1(=[O:39])[N:1]([C@H:2]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]12

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 7131803methyl (3S)-3-amino-3-(3,4-dimethoxyphenyl)propanoate

Product 1

HCID 9951198Methyl (S)-3-phthalimido-3-(3,4-dimethoxyphenyl)propionate

Procedure

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) were allowed to react according to the procedure of Example 85. 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, 4H, Ar), 6.80-7.10 (m, 3H, Ar), 5.65 (dd, 1H, J1 =7 Hz, J2 =9 Hz), 3.73 (s, 3H, OCH3), 3.72 (s, 3H, OCH3), 3.55 (s, 3H, OCH3), 3.30-3.67 (m, 2H); 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

  1. customto react

Sources & evidence

ORD record
ord-9696f884131b4956a4a6e0c5b83b86be
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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