Lithium Hydroxide → 4-Benzyl-5-(2-carboxy-4-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 987918

Reaktionsgleichung

Reaktionsgleichung von HRID 987918
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH:22]2[C:28]([O:30]C)=[O:29])[O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH:22]2[C:28]([OH:30])=[O:29])[O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 698547414-Benzyl-5-(2-methoxycarbonyl-4-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 700346664-Benzyl-5-(2-carboxy-4-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-benzyl-5-(2-methoxycarbonyl-4-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.81 g, 3.94 mmol) in dry tetrahydrofuran (24 ml) was treated with 1M aqueous lithium hydroxide solution (8 ml 7.88 mM). The resulting mixture was stirred at room temperature for 6 hours then diluted with ethyl acetate, washed with a 1:1 mixture of brine and 1 M hydrochloric acid, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 4-benzyl-5-(2-carboxy-4-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.66 g, 95%) as a yellow oil which was used in the next step without further purification.

Aufarbeitung

  1. washwashed with a 1:1 mixture of brine and 1 M hydrochloric acid
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdc57423c70841e8b9141bbf981ccef5
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632826B1

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