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Sodium Hydroxide → 4-(3-(3-(Tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy)butanoic acid

HRID 1014648
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Reaktionsgleichung

Reaktionsgleichung von HRID 1014648
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[O:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[O:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[OH:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67317450HCID 67317450, Verbindung

Produkt 1

HCID 673166134-(3-(3-(Tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the ester 130 (2.3 g, 6.0 mmol) in THF (80 mL) and MeOH (20 mL) was added NaOH solution (8 mL, 2N). The resulting mixture was stirred at room temperature for overnight following which the solvent was removed under reduced pressure and pH adjusted to 6 by the addition of cold dilute HCl. This was then extracted with DCM. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 4-(3-(3-(tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy) butanoic acid (131). The product was directly utilized for the next transformation. Yield (1.94 g, 91%): 1H NMR (400 MHz, CDCl3) δ 7.18-7.22 (m, 1H), 6.84-6.90 (m, 2H), 6.77 (dd, J=7.6, 1.6 Hz, 1H), 5.18 (bs, 1H), 4.48-4.53 (m, 1H), 3.96 (t, J=6.4 Hz, 2H), 2.93-2.99 (m, 2H), 2.38 (t, J=7.4 Hz, 2H), 1.90-1.96 (m, 2H), 1.64-1.71 (m, 2H), 1.45 (s, 9H).

Aufarbeitung

  1. customwas removed under reduced pressure
  2. additionpH adjusted to 6 by the addition of cold dilute HCl
  3. extractionThis was then extracted with DCM
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d77114975c464b33a75fcf6085a149e4
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07982071B2

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