Sodium Carbonate → HCID 9949781, Verbindung

HRID 1940064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940064
Cl.[CH3:2][O:3][C:4](=[O:16])[CH2:5][CH:6]([NH2:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(OCC)=O>O.C(#N)C>[C:29]1(=[O:38])[N:15]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH2:5][C:4]([O:3][CH3:2])=[O:16])[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 21845164Benzenepropanoic acid, β-amino-4-methoxy-, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 9949781HCID 9949781, VerbindungAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-amino-3-(4-methoxyphenyl)propionic acid methyl ester hydrochloride (1.50 g, 6.1 mmol) and sodium carbonate (90.65 g, 6.1 mmol) in 40 mL of water was added N-carboethoxyphthalimide (1.34 g, 6.1 mmol) in 12 mL of acetonitrile. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partially concentrated and this mixture was stirred for 72 hours. The resulting slurry was filtered and the solid was washed with copious amount of water. The solid was dried in vacuo (30° C., <1 mm) to afford 1.70 g (50%) of methyl 3-phthalimido-3-(4-methoxyphenyl)propionate as a white powder. mp 65°-66° C.; 1H NMR (DMSO-6, 250 MHz) δ7.83-7.91 (m, 4H), 6.88-7.3 (m, 4H), 5-80 (dd, 1H, J=7.5, 2.5), 372 (S, 3H), 3.54 (3, 3H), 3.2-3.6 (m, 2H); 13C NMR (DMSO-d6) δ170.7, 167.5, 158.7, 134.6, 131.0, 130.5, 128.3, 123.2, 113.9, 55.0, 51.5, 49.4, 35.4. Anal. Calcd for C19H17NO5 : C, 67.25; H, 5.05; N, 4.13; Found: C, 66.96; H, 5.00; N, 4.11.

Aufarbeitung

  1. concentrationThe reaction mixture was partially concentrated
  2. stirringthis mixture was stirred for 72 hours
  3. filtrationThe resulting slurry was filtered
  4. washthe solid was washed with copious amount of water
  5. customThe solid was dried in vacuo (30° C., <1 mm)

Quellen und Nachweise

ORD-Eintrag
ord-0e599b125c9f425391387ca6777fe73e
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698579

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