Benzenesulfonyl chloride → Phenylsulfonylhomophenylalanine

HRID 378329Notes

Reaction equation

HRID 378329 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 21967295PhenylsulfonylhomophenylalanineYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5bf0d2c730b443f18867ef201225f361
Source dataset
uspto-grants-2000_02
Patent number
US06030946

Reaction notes

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