Water → 2-(3,4-Bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)acetic acid

HRID 1478885

Reaktionsgleichung

Reaktionsgleichung von HRID 1478885
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].[C:25]([O-:28])([O-])=[O:26].[K+].[K+].O>CN(C=O)C.CO.[OH-].[Na+].Cl.C1COCC1>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:15][CH2:16][NH:17][C:25]([O:28][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Komponenten

10

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 11008556Methyl 3,4-Dihydroxyphenylacetate

Produkt 1

HCID 867252812-(3,4-Bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To methyl 2-(3,4-dihydroxyphenyl)acetate (1.0 g) in DMF (10 mL) was added tert-butyl 2-bromoethylcarbamate (2.7 g) and K2CO3 (1.7 g). The resulting reaction mixture was stirred at 60° C. overnight. Water was added and the aqueous phase extracted with EtOAc. The organic phase was then dried and concentrated. The residue was purified by flash chromatography. The product was obtained as a mixture of mono- and bis-alkylation. The mixture was then dissolved in MeOH and THF (10 mL, 1:1) and IN NaOH was added. The resulting reaction mixture was stirred at room temperature overnight. IN HCl was added to acidify the solution. The aqueous phase was extracted with EtOAc (3×). The organic phases were combined, dried and concentrated. The title product was obtained by reverse phase chromatography purification (0.5 g).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionthe aqueous phase extracted with EtOAc
  3. customThe organic phase was then dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. customThe product was obtained as a mixture of mono- and bis-alkylation
  7. customThe resulting reaction mixture
  8. stirringwas stirred at room temperature overnight
  9. extractionThe aqueous phase was extracted with EtOAc (3×)
  10. customdried
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c12e81b672324999a5c61d59ee958931
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403850B2

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