2-Naphthalenesulfonyl chloride → N-[(benzyloxy)carbonyl]-3-(2-naphthylsulfonamido)-L-alanine

HRID 257282Notes

Reaction equation

HRID 257282 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].[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:22][C:23]([NH:25][C@H:26]([C:29]([OH:31])=[O:30])[CH2:27][NH2:28])=[O:24])=[CH:17][CH:16]=1>CCOCC.[OH-].[Na+]>[CH2:21]([O:22][C:23]([NH:25][C@H:26]([C:29]([OH:31])=[O:30])[CH2:27][NH:28][S:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:13])=[O:12])=[O:24])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 2756313Z-Dap-OH

Product 1

HCID 53772217N-[(benzyloxy)carbonyl]-3-(2-naphthylsulfonamido)-L-alanineYield 66.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 21.4 g of 2-naphthylsulfonyl chloride in 200 ml of ether is added dropwise while stirring to a solution of 15 g of N-α-Z-L-2,3-diaminopropionic acid in 189 ml of 1N sodium hydroxide solution. The mixture is left to stir for a further 6 hours. Subsequently, the reaction mixture is poured into ice-cold 2N hydrochloric acid and extracted with ethyl acetate. The organic is washed with water, dried and evaporated. After chromatography of the residue on silica gel with methylene chloride/methanol/acetic acid (94:5:1) there are isolated 17.9 g of N-[(benzyloxy)carbonyl]-3-(2-naphthylsulfonamido)-L-alanine.

Workup

  1. waitThe mixture is left
  2. extractionextracted with ethyl acetate
  3. washThe organic is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dcdc5cc7bc294176b365c0c451971b02
Source dataset
uspto-grants-1993_11
Patent number
US05260307

Reaction notes

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