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

HRID 487222ノート

反応式

HRID 487222 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21873804Tetrahydrofuran ethanol溶媒2 回

実験手順

To a stirred suspension of 4-biphenyl-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.

後処理

  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

出典と根拠

ORDレコード
ord-c5fc5633de0a4753bfdd5e7d70a9820e
出典データセット
uspto-grants-1994_03
特許番号
US05294632

反応ノート

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