2-Naphthalenesulfonyl chloride → N-(2-naphthylsulfonyl)-D-phenylalanine

HRID 234846Notes

Reaction equation

HRID 234846 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].[NH2:15][C@@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.[OH-].[Na+]>[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:15][C@@H:16]([C:24]([OH:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 71567D-Phenylalanine

Product 1

HCID 1115233N-(2-naphthylsulfonyl)-D-phenylalanineYield 91.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

20 g of 2-naphthylsulphonyl chloride in 150 ml of ether are added to a solution of 7.3 g of (R)-phenylalanine in 120 ml of 1N sodium hydroxide solution. The reaction mixture is stirred for 15 hours and decanted. The aqueous phase is separated, washed with ether, acidified to pH 3 with HCl and extracted with ethyl acetate. The organic phase is dried and evaporated. The separated crystals are suspended in ether and filtered off. There are obtained 14.4 g of N-(2-naphthylsulfonyl)-3-phenyl-D-alanine, m.p. 146° C.

Workup

  1. customdecanted
  2. customThe aqueous phase is separated
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. customevaporated
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-9b78baaa45994cc184ca00104b1041e3
Source dataset
uspto-grants-1997_01
Patent number
US05595999

Reaction notes

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