Lithium Hydroxide → {[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid

HRID 1665261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665261
C([O:3][C:4](=[O:35])[CH2:5][N:6]([C:8](=[O:34])[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=3[O:32][CH3:33])=[CH:20][CH:19]=2)[CH:10]=1)[CH3:7])C.[OH-].[Li+]>C1COCC1>[F:31][C:27]1[C:28]([F:30])=[CH:29][C:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=3[F:15])[C:8]([N:6]([CH2:5][C:4]([OH:35])=[O:3])[CH3:7])=[O:34])=[CH:23][CH:22]=2)=[C:25]([O:32][CH3:33])[CH:26]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67152333{[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid ethyl ester

Produkt 1

HCID 52933063{[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

{[3-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid ethyl ester (0.29 g, 0.59 mmol) was dissolved in THF (25 mL) and lithium hydroxide solution (0.5N, 2 mL) was added. The mixture was stirred at room temperature for 2 hrs. Solvents were evaporated and the residue was treated with dilute hydrochloric acid and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Solvent was evaporated and the residue was dissolved in acetonitrile (1 mL) and diluted with water (8 mL). The mixture was lyophilized to give a fluffy solid as {[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid (0.26 g, 96%). HRMS (ES) calculated for C24H20F3NO5, 482.1186; found m/z 482.1185 [M+Na]+; 1H-NMR (DMSO-d6) δ ppm 12.86 (br s, 1H), 7.29-7.69 (m, 6H), 7.24 (dd, J=13.0, 7.2 Hz, 1H), 7.08 (d, J=8.5 Hz, 2H), 5.19 and 5.23 (s, 2H, rotamer), 3.97 and 4.14 (s, 2H, rotamer), 3.76 (s, 3H), 2.94 and 2.95 (s, 3H, rotamer).

Aufarbeitung

  1. customSolvents were evaporated
  2. additionthe residue was treated with dilute hydrochloric acid and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent was evaporated
  6. dissolutionthe residue was dissolved in acetonitrile (1 mL)
  7. additiondiluted with water (8 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5ba2498d5a1648dd9ab145a4d081e832
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039495B2

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