Hydrochloric Acid → 4-(2-Tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acid

HRID 981273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981273
[C:1]([O:5][C:6]([N:8]([CH2:13][CH:14]1[CH2:16][CH:15]1[C:17]1[C:27]([F:28])=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[C:19]([F:29])[C:18]=1[F:30])C(OC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>C(O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:13][CH:14]1[CH2:16][CH:15]1[C:17]1[C:27]([F:28])=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[C:19]([F:29])[C:18]=1[F:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15136265ethyl 4-[2-(N-tert-butoxycarbonyl-N-methoxycarbonylaminomethyl)cyclopropyl]-2,3,5-trifluorobenzoate

Produkt 1

HCID 151362664-(2-Tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acidAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 60 ml of ethanol was dissolved 5.22 g of ethyl 4-[2-(N-tert-butoxycarbonyl-N-methoxycarbonylaminomethyl)cyclopropyl]-2,3,5-trifluorobenzoate. To the resulting solution was added 60 ml of a 1N aqueous sodium hydroxide solution. The resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 60 ml of water and the resulting mixture was adjusted to pH 8 with 6N hydrochloric acid. Then, 150 ml of ethyl acetate was added thereto. The aqueous layer was separated and 100 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 4.10 g (98.1%) of 4-(2-tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acid.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. addition100 ml of ethyl acetate was added
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c61ad46d948040cfadcd7653bd7a1cf0
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990508

Notizen zur Reaktion

Wird geladen…