Lithium hydroxide, monohydrate → (1R,2R)-2-(4-Bromophenyl)-1-((S)-1-(tert-butoxycarbonyl)piperidine-2-carboxamido)cyclopropanecarboxylic Acid

HRID 600312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600312
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@:9]2([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:10][C@:9]2([NH:15][C:16]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:17])[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 57999639(S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate

Produkt 1

HCID 57999663(1R,2R)-2-(4-Bromophenyl)-1-((S)-1-(tert-butoxycarbonyl)piperidine-2-carboxamido)cyclopropanecarboxylic AcidAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)-cyclopropylcarbamoyl)piperidine-1-carboxylate (3 g) in THF (45 mL) and water (30 mL) was added lithium hydroxide monohydrate (0.298 g). The mixture was stirred at RT for 2 h. The mixture was partitioned between 0.1 N HCl(aq) and ethyl acetate, and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated in vacuo to leave the title compound (2.90 g) as a white solid.

Aufarbeitung

  1. customThe mixture was partitioned between 0.1 N HCl(aq) and ethyl acetate
  2. extractionthe aqueous phase was extracted twice more with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7bdb20dbd7cd4cf78ea8361174e6a0b4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902181B2

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