4-Toluenesulfonyl chloride → N-(toluene-4-sulfonyl)-N-methylphenylalanine

HRID 411261

反応式

HRID 411261 の反応式
[CH3:1][NH:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1CCOCC1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>[OH-].[Na+]>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([N:2]([CH3:1])[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 312751,4-DioxaneHCID 6951135N-Methylphenylalanine

生成物 1

HCID 12069251N-(toluene-4-sulfonyl)-N-methylphenylalanine収率 45.6%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

N-Methyl-L-phenylalanine (500 mg, 2.79 mmol) was dissolved in 1N NaOH (6 mL). Dioxane (9 mL)) was added, followed by p-toluenesulfonyl chloride (532 mg, 2.79 mmol) and the mixture was vigorously stirred for 1 hr. The volatiles were removed in vacuo and the residue was dissolved in water (30 mL) and washed with Et2O (2×30 mL) before making acidic with 1N HCl. The mixture was extracted with CHCl3 (3×30 mL) and the extracts were evaporated in vacuo to give N-(toluene-4-sulfonyl)-N-methylphenylalanine as a solid (424 mg, 45%). N-(Toluene-4-sulfonyl)-N-methylphenylalanine was coupled to L-phenylalanine ethyl ester using the procedure described in Method 3 (400 mg, 62%). The title compound was prepared via hydrolysis of the ethyl ester using NaOH in ethanol. Proton and carbon NMR analyis indicated a mixture of diastereomers.

後処理

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in water (30 mL)
  3. washwashed with Et2O (2×30 mL)
  4. extractionThe mixture was extracted with CHCl3 (3×30 mL)
  5. customthe extracts were evaporated in vacuo

出典と根拠

ORDレコード
ord-f9ebe3facdb3445495e5f2df29712911
出典データセット
uspto-grants-2003_05
特許番号
US06559127B1

関連ノート

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