Sodium Carbonate → HCID 9885548, compound

HRID 1531864Notes

Reaction equation

HRID 1531864 reaction equation
Cl.[CH2:2]([O:5][C:6](=[O:18])[CH2:7][CH:8]([NH2:17])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])(OCC)=O>O.C(#N)C>[C:31]1(=[O:40])[N:17]([CH:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:7][C:6]([O:5][CH2:2][CH2:3][CH3:4])=[O:18])[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 69868530HCID 69868530, compound

Product 1

HCID 9885548HCID 9885548, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-amino-3-(4-methoxyphenyl)propionic acid propyl ester hydrochloride (1.50 g, 5.52 mmol) and sodium carbonate (0.59 g, 5.52 mmol) in 50 mL of water was added N-carboethoxy-phthalimide (1.21 g, 5.52 mmol) in 12 mL of acetonitrile. The reaction was complete in one hour. The acetonitrile was removed in vacuo and 5 mL of ether was added to the mixture, which was stirred overnight at room temperature. The resulting slurry was filtered and the solid was washed with 60 mL of water. The solid was dried in vacuo (24° C., <1 mm) to afford 1.69 g (83.2%) of propyl 3-phthalimido-3-(4-methoxyphenyl)propionate as a white powder: mp 51.2-52.8° C.; 1H NMR (DMSO-d6 250 MHz) δ7.86 (m, 4H), 6.92-7.33 (m, 4H), 5.66 (dd, 1H, J1=7.5, 2.5 Hz), 3.90 (t, 2H, J=5 Hz), 3.72 (S, 3H), 3.3-3.63 (m, 2H), 1.42 (hex, 2H, J=7.5 Hz), 0.75 (t, 3H, J=7.5 Hz); 13C (DMSO-d6) δ170.2, 167.5, 158.7, 134.7, 131.0, 130.5, 128.3, 123.2, 113.9, 65.6; 55.0, 49.5, 21.3, 9.98. Anal. Calcd for C19H17NO5: =C, 68.65; H, 5.76; N, 3.81; Found=C, 68.42; H, 5.49; N, 3.76.

Workup

  1. customThe acetonitrile was removed in vacuo and 5 mL of ether
  2. additionwas added to the mixture, which
  3. filtrationThe resulting slurry was filtered
  4. washthe solid was washed with 60 mL of water
  5. customThe solid was dried in vacuo (24° C., <1 mm)

Sources & evidence

ORD record
ord-73546638171d44d08ac5640c108e9cd2
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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