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

HRID 29314

反応式

HRID 29314 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-4b1a9f1f172a4d3c90c461b5ee9970d7
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

関連ノート

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