Hydrochloric Acid → [3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester

HRID 1069648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069648
[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[C:14]2[CH2:27][C:28]([O:30]CC)=O)(=[O:6])[O:4][CH3:5].[Al]([NH2:36])(C)C.O.Cl>C1(C)C=CC=CC=1.C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:15]=[C:14]2[CH2:27][C:28]([NH2:36])=[O:30])(=[O:6])[O:4][CH3:5]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10813793[3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl esterHCID 16689643Aminodimethyl aluminium

Produkt 1

HCID 10550559[3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 160055Benzene, mixed with toluene, dealkylation productLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

[3-[[3-(2-Ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester (590 mg, 1.3 mmol) was dissolved in 40 mL of toluene and 10 mL of 0.67M (CH3)2AlNH2 in benzene/toluene were added. The mixture was heated at 50° C. for 3.25 hours and water and 1N HCl added. The mixture was extracted with a large volume of ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with a gradient, 1% MeOH/methylene chloride→4% MeOH/methylene chloride, to give 450 mg (80% yield) of [3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester.

Aufarbeitung

  1. extractionThe mixture was extracted with a large volume of ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica gel eluting with a gradient, 1% MeOH/methylene chloride→4% MeOH/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-182ae11f6e2047e297a9af07711b2189
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06252084B1

Notizen zur Reaktion

Wird geladen…