Potassium Hydroxide → [4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid

HRID 132567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132567
C[O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:7]=1.[OH-].[K+]>CO>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:24])=[O:2])=[CH:11][CH:10]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 21031129[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid methyl ester

Produkt 1

HCID 22054428[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acidAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of [4-(4-tert-butoxycarbonylaminobutyl)phenoxy]acetic acid methyl ester 32 (1.28 g, 3.78 mmol) in methanol (80 mL) was added with crushed potassium hydroxide (2.50 g, 85%, 37.8 mmol) and the mixture was stirred at room temperature for 5 h. Solvent was removed by rotary evaporation. The residue was taken up in water and acidified to pH 1 with 6N aqueous HCl, and extracted with dichloromethane. The combined organics were washed with brine, dried over Na2SO4, and concentrated to complete dryness to afford the desired product 33 as a white solid (1.19 g, 97% yield). 1H NMR (300 MHz, CD3OD) δ 1.41 (s, 9H), 1.42-1.70 (m, 4H), 2.45-2.60 (m, 2H), 3.00-3.20 (m, 2H), 4.60 (s, 2H), 6.80 (d, 2H), 7.08 (d, 2H). m/z (ESI): 322 [C17H25NO5—H]−.

Aufarbeitung

  1. customSolvent was removed by rotary evaporation
  2. extractionextracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b22610ff3b0f46b8a60551c3782922f6
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388013B2

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