Hydrochloric Acid → 2-Amino-2-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-propane-1,3-diol hydro-chloride

HRID 1865144

Reaktionsgleichung

Reaktionsgleichung von HRID 1865144
CC1[O:3][CH2:4][C:5]([CH2:26][OH:27])([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:11][CH:10]=2)[N:6]=1.[ClH:28]>C(O)C>[ClH:28].[NH2:6][C:5]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:11][CH:10]=1)([CH2:26][OH:27])[CH2:4][OH:3]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 66768869(2-Methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

Produkt 1

HCID 667683152-Amino-2-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-propane-1,3-diol hydro-chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (300 mg, 1.27 mmol) in DMF (5 ml) was added Cs2CO3 (1.2 g, 3.83 mmol) and (3-bromo-propoxy)-benzene (273 mg, 1.27 mmol). The reaction mixture was stirred at 85° C. for 4 hours. AcOEt and water were then added, the organic layer was separated and the aqueous phase was extracted with AcOEt (3×50 ml). The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (AcOEt/Hexane 9:1) affords (2-methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol as colorless oil. To a solution of (2-methyl-4-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol (50 mg, 0.135 mmol) in ethanol (2 ml) was added conc. HCl (2 ml). The reaction mixture was stirred at 85° C. for 2 hours, then concentrated to dryness. The residue was re-dissolved in AcOEt and precipitated with hexanes. The solid was filtered off, washed with dry ether and dried in vacuo to afford 2-amino-2-{2-[4-(3-phenoxy-propoxy)-phenyl]-ethyl}-propane-1,3-diol hydro-chloride as a colorless powder. ESI+ MS: m/z=370.4 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was re-dissolved in AcOEt
  3. customprecipitated with hexanes
  4. filtrationThe solid was filtered off
  5. washwashed with dry ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-01434692f82c490e819caecbf0bd59c9
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625950B2

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