Water → 3-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid

HRID 901947

Reaktionsgleichung

Reaktionsgleichung von HRID 901947
O.[OH-].[Li+].O.[CH3:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]C)=[O:22])[CH:16]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]>O1CCOCC1>[C:21]([C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:6]([CH3:5])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10])([OH:23])=[O:22]

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59700597Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

Produkt 1

HCID 224502433-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (420 mg, 10 mmol) and water (15 ml) were added to a solution of tert-butyl N-methyl-N-(3-(methyloxycarbonyl)benzyl)carbamate (1.6 g, 5.6 mmol) in dioxan (20 ml) and the mixture was stirred for 2 h. The dioxan was removed in vacuo and the residue was taken up in 0.3N potassium hydrogen sulphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water and brine, dried and reduced to afford tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (1.4 g, 95%).

Aufarbeitung

  1. customThe dioxan was removed in vacuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water and brine
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bfed7b5070074d4db80fec8494a809e6
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365065B2

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