Lithium Hydroxide → 6-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid

HRID 417730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417730
C([O:3][C:4]([CH:6]1[CH2:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[O:8][N:7]1[C:14](=[O:24])[CH:15]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]([CH3:18])[CH3:17])=[O:5])C.[OH-].[Li+]>C(O)C>[CH3:23][O:22][C:20]([NH:19][CH:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[CH2:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[O:8]1)=[O:24])=[O:21]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 666206496-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester

Produkt 1

HCID 666210856-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 6-(2-methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester (1.31 g, 3.83 mmol) in ethanol (10 mL) was added a solution of lithium hydroxide (1M in water, 7.6 mL, 7.6 mmol). The reaction was stirred at room temperature for 30 minutes. The reaction was partially concentrated and the resulting aqueous solution was washed with ethyl acetate. The ethyl acetate layer was discarded and the aqueous layer was acidified using concentrated HCl. The acidic aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to yield crude 6-(2-methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid, which was used without further purification.

Aufarbeitung

  1. concentrationThe reaction was partially concentrated
  2. washthe resulting aqueous solution was washed with ethyl acetate
  3. extractionThe acidic aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-941fa3982e2347c4b838d33496df1d6a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

Notizen zur Reaktion

Wird geladen…