Hydrogen Bromide → HCID 178510788、化合物

HRID 1462491ノート

反応式

HRID 1462491 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 178510788HCID 178510788、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7bc8d160f3574be98f3d9a2cd7ce787d
出典データセット
uspto-grants-1984_07
特許番号
US04460579

反応ノート

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