Benzenesulfonyl chloride → Phenylsulfonylhomophenylalanine

HRID 378329ノート

反応式

HRID 378329 の反応式
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:16]1([S:22]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2 回HCID 2724505(S)-2-amino-4-phenylbutanoic acid

生成物 1

HCID 21967295Phenylsulfonylhomophenylalanine収率 70%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a suspension of homophenylalanine (Synthetech) (7 g, 39.1 mmol) in distilled water (21.5 mL) was added a 2 M aqueous NaOH (21.5 mL). After 5 minutes, the suspension had cleared and phenylsulfonyl chloride (5.48 mL, 43 mmol) was added. After 2 hours, the reaction mixture's pH was adjusted to 12 with 2 M aqueous NaOH (5 mL), and extracted with Et2O (2×100 mL). The aqueous layer's pH was adjusted to 1 with 6 M HCl (10 mL), and the product was extracted with EtOAc (100 mL), dried over MgSO4 filtered, and the solvent was removed under reduced pressure. The residue was triturated with Et2O (2×100 mL), filtered, and pumped to dryness, giving 8.74 g (70%) of phenylsulfonylhomophenylalanine.

後処理

  1. waitAfter 2 hours
  2. extractionextracted with Et2O (2×100 mL)
  3. extractionthe product was extracted with EtOAc (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was triturated with Et2O (2×100 mL)
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-5bf0d2c730b443f18867ef201225f361
出典データセット
uspto-grants-2000_02
特許番号
US06030946

反応ノート

読み込み中…