Lithium Hydroxide → 3-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid

HRID 1810438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810438
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:14][CH3:15])[CH:6]=1)C.[Li+].[OH-]>CO>[CH2:19]([O:18][C:16]([N:13]([CH2:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Br:11])[C:4]([OH:26])=[O:3])[CH2:14][CH3:15])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 574198633-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid ethyl ester

Produkt 1

HCID 574198643-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid ethyl ester (3.62 g, 7.2 mmol) was dissolved in MeOH (40 mL) and cooled to 0° C. 1N Aqueous LiOH (22 mL, 22 mmol) was added, and the reaction was stirred at room temperature for 3 hours. The mixture was quenched with 1N aqueous HCl (22 mL) and extracted three times with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to give the title compound, which was combined with the hydrolyzed product isolated in step 5.

Aufarbeitung

  1. customThe mixture was quenched with 1N aqueous HCl (22 mL)
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1eea093de6e6480289b49975d092eb1c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362044B2

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