4-Nitrobenzenesulfonyl chloride → (s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

HRID 548228

反応式

HRID 548228 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20]>O.O1CCOCC1>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:11][C@@H:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:8]([OH:10])=[O:9])(=[O:30])=[O:29])=[CH:26][CH:27]=1)([O-:21])=[O:20]

参加物

6

反応物 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 99291L-Phenylglycine

生成物 1

HCID 362697(s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution of L-phenylglycine (0.227 g, 1.5 mmol) in water (5 ml) and dioxane (5 ml) was added triethylamine (0.42 ml, 3.0 mmol) followed by slow addition of 4-nitrobenzene sulphonyl chloride (0.5 g, 2.3 mmol) in dioxane (5 ml) at 0° C. After stirring for 45 minutes the reaction mixture was evaporated to dryness, re-dissolved in EtOAc and washed with saturated NaHCO3 solution (2×20 ml) and water (10 ml). The EtOAc layer was dried over Na2SO4, filtered and evaporated to dryness. LCMS purity 75%, (molecular ion not observed) yield 0.58 g, (76%). This material was used without any purification.

後処理

  1. customwas evaporated to dryness
  2. dissolutionre-dissolved in EtOAc
  3. washwashed with saturated NaHCO3 solution (2×20 ml) and water (10 ml)
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThis material was used without any purification

出典と根拠

ORDレコード
ord-e6c50959d0094ca88cc7a704e2bf1aef
出典データセット
uspto-grants-2011_05
特許番号
US07939666B2

関連ノート

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