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

HRID 1583951노트

반응식

HRID 1583951 반응식
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]

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 13145060HCID 13145060, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-48ca72d97fbc4bf0a523e32c73a2578a
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04555506

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