Benzenesulfonyl chloride → Phenylsulfonylhomophenylalanine

HRID 378329노트

반응식

HRID 378329 반응식
[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

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2회HCID 2724505(S)-2-amino-4-phenylbutanoic acid

생성물 1

HCID 21967295Phenylsulfonylhomophenylalanine수율 70%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5bf0d2c730b443f18867ef201225f361
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030946

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