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

HRID 1374602Notes

Reaction equation

HRID 1374602 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 12069251N-(toluene-4-sulfonyl)-N-methylphenylalanineYield 45.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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 CHCl (3×30 mL) and the extracts were evaporated in vacuo to give N-(toluene-4-sulfonyl)-N-methylphenylalanine as a solid (424 mg, 45%).

Workup

  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 CHCl (3×30 mL)
  5. customthe extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-241281b25c8d4d6d9931d74a9e0aec7e
Source dataset
uspto-grants-2007_01
Patent number
US07166580B2

Reaction notes

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