Triethylamine → N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-D-valine

HRID 29314

Reaction equation

HRID 29314 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)CC)C>O1CCOCC1.O>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 71563D-ValineHCID 27601854'-Nitrobiphenyl-4-sulfonyl chloride

Product 1

HCID 68708071N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-D-valineYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To 0.117 g of D-valine in 2.5 mL dioxane and 2.5 mL of water, cooled in an ice bath, was added 0.31 g of 4′-nitro-1,1′-biphenyl-4-sulfonyl chloride, followed by 0.4 mL of triethylamine, The reaction was then stirred at room temperature overnight. After concentrating the reaction mixture in vacuo, the residue was extracted with ethyl acetate and 1N HCl. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 0.35 g of N-[(4′-nitro-1,1′-biphenyl-4-yl)sulfonyl]-D-valine as a solid. Yield 74.5%. m.p. 165-167° C.; MS: 377.0 (M−H)−.

Workup

  1. concentrationAfter concentrating the reaction mixture in vacuo
  2. extractionthe residue was extracted with ethyl acetate and 1N HCl
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b1a9f1f172a4d3c90c461b5ee9970d7
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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