Malonic Acid → 3-Amino-3-{3-[(propan-2-yl)oxy]phenyl}propanoic acid

HRID 501733

Reaktionsgleichung

Reaktionsgleichung von HRID 501733
FC(F)(F)C([NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=2)[C@H:8]([OH:19])[CH2:7]1)=O.C([O:25]C1C=C(C=CC=1)C=O)(C)C.C(O)(=O)CC(O)=O.C([O-])(=O)C.[NH4+]>C(O)C.CO.C(Cl)Cl>[NH2:5][CH:6]([C:14]1[CH:9]=[CH:10][CH:11]=[C:12]([O:15][CH:16]([CH3:17])[CH3:18])[CH:13]=1)[CH2:7][C:8]([OH:19])=[O:25]

Komponenten

7

Edukt 4

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 7129143-IsopropoxybenzaldehydeHCID 594236882,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-isopropoxy-2,3-dihydro-1H-inden-1-yl)acetamide

Produkt 1

HCID 230026273-Amino-3-{3-[(propan-2-yl)oxy]phenyl}propanoic acidAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Step AU (2). A solution of 3-isopropoxybenzaldehyde (77 g, 470 mmol), malonic acid (52 g, 496 mmol) and ammonium acetate (65 g, 844 mmol) in 1.0 L of ethanol was refluxed at 120° C. for 24 h. The solvent was evaporated in vacuo. The residue was purified using silica-gel column chromatography with (100% EtOAc, then 30% methanol/methylene chloride) to afford 65 g (62% yield) of 3-amino-3-(3-isopropoxyphenyl)propanoic acid as a white solid. LC-MS (M+H)+=224.14. 1H NMR (300 MHz, DMSO-d6) δ 1.2-1.3 (d, 6H) 2.4-2.5 (m, 2H) 4.2-4.4 (m, 1H) 4.5-4.7 (m, 1H) 6.8-6.9 (m, 1H) 6.9-7.0 (m, 2H) 7.2-7.3 (m, 1H).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-76c2b766ae6547b9ae706f38eaa98013
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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