L-Phenylalanine → 2-[(2-naphthylsulfonyl)amino]-3-phenylpropanoic acid

HRID 565583Notes

Reaction equation

HRID 565583 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[OH-].[Na+].[NH2:17][C@H:18]([C:26]([OH:28])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:17][CH:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]([OH:28])=[O:27])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 6140L-PhenylalanineHCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 31259092-[(2-naphthylsulfonyl)amino]-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.6 mmol (1.71 g) of 2-naphthylsulphonyl chloride in 10 ml of dichloro-methane and a solution of 7.9 mmol (0.32 g) of sodium hydroxide in 10 ml of water are added slowly in succession to 7.6 mmol (1.25 g) of phenylalanine and 7.6 mmol (0.3 g) of sodium hydroxide in 10 ml of water. The reaction mixture is stirred for 1 hour at room temperature. After decanting, the aqueous phase is washed with dichloromethane and rendered acidic to pH=2 with a dilute hydrochloric acid solution. After extraction with dichloromethane, the organic phase is dried over sodium sulphate and concentrated to yield the expected product.

Workup

  1. customAfter decanting
  2. washthe aqueous phase is washed with dichloromethane
  3. extractionAfter extraction with dichloromethane
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecabe397ce0a48ecbb671ddf5c3bfc5b
Source dataset
uspto-grants-2001_01
Patent number
US06172108B2

Reaction notes

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