Hydrochloric Acid → 1-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid

HRID 504340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504340
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:18][C:19]([NH2:21])=[O:20].C(O)C.[OH-].[Li+].Cl>C(OCC)(=O)C.CO.C1COCC1>[NH2:21][C:19]1[O:20][CH:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([C:11]3([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]3)=[CH:9][CH:10]=2)[N:18]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 3939Lithium HydroxideHCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Produkt 1

HCID 666616511-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate (0.20 g, 0.00079 mol, example 243, steps 1 & 2) and urea (0.095 g, 0.0016 mol) in ethanol (5.0 mL, 0.086 mol) was refluxed overnight. The mixture was diluted with ethyl acetate and washed with sat'd. NaHCO3, brine, dried and concentrated. The methyl ester was purified by CombiFlash using CH2Cl2/EtOAc (max. EtOAc 100%). The ester was hydrolyzed using lithium hydroxide (6.0 eq.) in methanol/THF and then acidified by adding 1 N HCl. The solvent was removed under vacuum and the crude product was used in the next step. LC-MS: 259.2 (M+H+) methyl eater; 245.2 (M+H+) acid

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. washwashed with sat'd
  3. dry with materialNaHCO3, brine, dried
  4. concentrationconcentrated
  5. customThe methyl ester was purified by CombiFlash
  6. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6e3ebcb8abbb40a783a0eb1eb4277d61
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776874B2

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