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

HRID 29314

반응식

HRID 29314 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-4b1a9f1f172a4d3c90c461b5ee9970d7
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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