Lithium Hydroxide → {(S)-1-tert-Butoxycarbonyl-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-acetic acid

HRID 1963071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963071
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[CH3:39])=[O:15])[CH2:10][C@@H:9]1[CH2:40][C:41]([O:43]C)=[O:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[CH3:39])=[O:15])[CH2:10][C@@H:9]1[CH2:40][C:41]([OH:43])=[O:42])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67772153(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-methoxycarbonylmethyl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 70663959{(S)-1-tert-Butoxycarbonyl-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-acetic acidAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the compound of step 4 (1.40 g, 2.33 mmol) in 15.5 ml of dioxane was added 3.5 ml of a 1 M aqueous solution of lithium hydroxide and the mixture was heated at 50° C. for 1 h. The solvents were evaporated under reduced pressure and the residue was dissolved in 45 ml of water. The solution was cooled to 0° C. and acidified to pH 2 with 5 N hydrochloric acid. The obtained suspension was extracted with EA and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. 1.37 g of the title compound were obtained as a green solid melting at 103-105° C.

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 45 ml of water
  3. temperatureThe solution was cooled to 0° C.
  4. extractionThe obtained suspension was extracted with EA
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f8f47d30e0c441308698c1a957c8f282
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415336B2

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