Hydrogen Bromide → HCID 178510788, Verbindung

HRID 1462491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462491
CC1C=CC(S([NH:11][CH:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13][P:14](=O)([O:18]CC)[O:15]CC)(=O)=O)=CC=1.C1(O)C=CC=CC=1.Br.NC(CC1C=CC=CC=1)CP(=O)(O)O.[NH4+].[OH-].O>O.C(O)(C)C>[NH2:11][CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][PH:14](=[O:15])[OH:18]

Komponenten

8

Edukt 5

HCID 260Hydrogen BromideHCID 996PhenolHCID 12749378(2-Amino-3-phenylpropyl)phosphonic acidHCID 13145060HCID 13145060, VerbindungHCID 86589665Water ammonium hydroxide

Produkt 1

HCID 178510788HCID 178510788, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of [2-[[(4-methylphenyl)sulfonyl]amino]-3-phenylpropyl]phosphonic acid, diethyl ester (5.9 g., 13.9 mmole), phenol (8.0 g., 85.1 mmole), and 48% aqueous hydrobromic acid (50 ml.) is refluxed for 5.5 hours. The cooled mixture is diluted with water (50 ml.) and washed with ethyl acetate (2×50 ml.). The aqueous phase is evaporated to dryness, taken up in water (30 ml.) and evaporated again. This is repeated twice more. Finally, the residue is taken up in water and applied to an AG 50 W-X2 (H+ form) column (60 ml. bed volume) and eluted first with water then with 5% pyridine-water. The fractions containing the desired product are combined and evaporated to dryness. The solid residue is triturated with acetonitrile to give 2.55 g. of (2-amino-3-phenylpropyl)phosphonic acid as an off-white crystalline solid; m.p. 347° (dec.); TLC (isopropanol/conc. NH4OH/water; 7:2:1) spot at Rf =0.27.

Aufarbeitung

  1. temperatureis refluxed for 5.5 hours
  2. washwashed with ethyl acetate (2×50 ml.)
  3. customThe aqueous phase is evaporated to dryness
  4. customevaporated again
  5. washeluted first with water
  6. additionThe fractions containing the desired product
  7. customevaporated to dryness
  8. customThe solid residue is triturated with acetonitrile
  9. customto give 2.55 g

Quellen und Nachweise

ORD-Eintrag
ord-7bc8d160f3574be98f3d9a2cd7ce787d
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460579

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