Lithium Hydroxide → (2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-methyl-4-oxo-4-pyrrolidin-1-ylbutanoic acid

HRID 2246242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246242
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16](=[O:22])[N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C@H:10]([CH3:15])[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16](=[O:22])[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)[C@H:10]([CH3:15])[C:11]([OH:13])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86617962Methyl (2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-methyl-4-oxo-4-pyrrolidin-1-ylbutanoate

Produkt 1

HCID 68431373(2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-methyl-4-oxo-4-pyrrolidin-1-ylbutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Step A (0.404 g, 1.29 mmol) in THF (30 mL) and water (10 mL) was added lithium hydroxide (96.0 mg, 4.0 mmol). After stirring at room temperature for 3 h, the reaction was quenched with 1N hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo to give the desired product.

Aufarbeitung

  1. customthe reaction was quenched with 1N hydrochloric acid
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with two portions of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1f03f7131a84ac4982ce4756bfe97be
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687492B2

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