Hydrogen Bromide → (2-Amino-3-phenylpropyl)phosphonic acid

HRID 1583951ノート

反応式

HRID 1583951 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:21])([O:18]CC)[O:15]CC)(=O)=O)=CC=1.C1(O)C=CC=CC=1.Br>O>[NH2:11][CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][P:14](=[O:15])([OH:21])[OH:18]

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 13145060HCID 13145060、化合物

生成物 1

HCID 12749378(2-Amino-3-phenylpropyl)phosphonic acid収率 85.3%

試薬・触媒・溶媒 1

HCID 962Water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.) was refluxed for 5.5 hours. The cooled mixture was diluted with water (50 ml.) and washed with ethyl acetate (2×50 ml.). The aqueous phase was evaporated to dryness, taken up in water (30 ml.) and evaporated again. This was repeated twice more. Finally, the residue was taken up in water and applied to an AG50W-X2 (H+ form) column (60 ml. bed volume) and eluted first with water then with 5% pyridine-water. The fractions containing the desired product were combined and evaporated to dryness. The solid residue was 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.); Rf (isopropanol/conc. NH4OH/water; 7:2:1)=0.27.

後処理

  1. temperaturewas refluxed for 5.5 hours
  2. washwashed with ethyl acetate (2×50 ml.)
  3. customThe aqueous phase was 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 was triturated with acetonitrile

出典と根拠

ORDレコード
ord-48ca72d97fbc4bf0a523e32c73a2578a
出典データセット
uspto-grants-1985_11
特許番号
US04555506

反応ノート

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