Triethylamine → 2-(Dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid

HRID 466226노트

반응식

HRID 466226 반응식
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8](=O)[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[CH3:19][O:20][P:21]([CH2:25][NH2:26])(=[O:24])[O:22][CH3:23].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C1COCC1.CCO.C1COCC1>[CH3:19][O:20][P:21]([CH2:25][NH:26][CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:2][CH:3]=1)[C:9]([OH:11])=[O:10])([O:22][CH3:23])=[O:24]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 13310504Dimethyl (aminomethyl)phosphonateHCID 139824372-Oxo-3-(4-phenylphenyl)propanoic acid

생성물 1

HCID 538116872-(Dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21873804Tetrahydrofuran ethanol용매2회

실험 절차

To a stirred suspension of 4-biphenylyl-pyruvic acid in anhydrous THF-EtOH (50 mL, 9:1) is added aminomethylphosphonic acid dimethyl ester (520 mg, 3.7 mmol) in THF-EtOH (5 mL, 9:1). The pH is then adjusted with triethylamine to 6.6. After 20 minutes, sodium cyanoborohydride (100 mg, 1.6 mmol) in THF (2.5 mL) is added over 30 minutes. The solution is stirred for 18 hours and then concentrated. Ether (20 mL) is added and the mixture is cooled and treated with 1N HCl (7 mL). After stirring at room temperature for 30 minutes, the solid is filtered off and washed with ether and water to yield 2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid as a waxy solid.

후처리

  1. concentrationconcentrated
  2. additionEther (20 mL) is added
  3. temperaturethe mixture is cooled
  4. additiontreated with 1N HCl (7 mL)
  5. stirringAfter stirring at room temperature for 30 minutes
  6. filtrationthe solid is filtered off
  7. washwashed with ether and water

출처 및 근거

ORD 기록
ord-88519e83c63b408b8575ff0238645112
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155100

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