Lithium Hydroxide → 2-((4-Phenylphenyl)formamido)acetic acid

HRID 1178007

Reaktionsgleichung

Reaktionsgleichung von HRID 1178007
[Li+].[OH-].C([O:5][C:6](=[O:23])[CH2:7][NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:10])C>C1COCC1.CO.O>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:16][C:11]([C:9]([NH:8][CH2:7][C:6]([OH:23])=[O:5])=[O:10])=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 2163299Ethyl 2-[(4-phenylphenyl)carbonylamino]acetate

Produkt 1

HCID 2629432-((4-Phenylphenyl)formamido)acetic acidAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

LiOH (1.111 g, 26.47 mmol) was added to a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid ethyl ester (5 g, 17.65 mmol) in THF:MeOH:H2O (3:1:1, 95 mL), and the resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated, and the residue was diluted with water (2 mL), acidified with citric acid solution and extracted with EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated in vacuo to obtain afford 3.892 g (86.3% yield) of [(biphenyl-4-carbonyl)-amino]-acetic acid. LCMS purity: 96.4%.

Aufarbeitung

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-7831997ee2a64ac0bb9a51ab34009eb1
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

Verknüpfte Notizen

Wird geladen…