Hydrogen Bromide → HCID 178510788, compound

HRID 1462491Notes

Reaction equation

HRID 1462491 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

HCID 178510788HCID 178510788, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7bc8d160f3574be98f3d9a2cd7ce787d
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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