Hydrogen Bromide → HCID 178510788, 화합물

HRID 1462491노트

반응식

HRID 1462491 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)([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]

참가 물질

8

반응물 5

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

생성물 1

HCID 178510788HCID 178510788, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

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.) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-7bc8d160f3574be98f3d9a2cd7ce787d
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04460579

반응 노트

불러오는 중…