4-Toluenesulfonyl chloride → N-(Toluene-4-sulfonyl)-L-prolyl-L-phenylalanine N-(Toluene4-sulfonyl)amide

HRID 1356870Notes

Reaction equation

HRID 1356870 reaction equation
[H-].[Na+].[C:3]1([CH3:31])[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:30][CH2:29][CH2:28][C@H:13]2[C:14]([NH:16][C@H:17]([C:25]([NH2:27])=[O:26])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C1COCC1>[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([NH:27][C:25](=[O:26])[C@H:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:16][C:14](=[O:15])[C@@H:13]2[CH2:28][CH2:29][CH2:30][N:12]2[S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH3:31])=[CH:4][CH:5]=2)(=[O:11])=[O:10])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 54382446N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide

Product 1

HCID 54500258N-(Toluene-4-sulfonyl)-L-prolyl-L-phenylalanine N-(Toluene4-sulfonyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(Toluene-4-sulfonyl)-L-proline was reacted with L-phenylalanine amide using the procedure described in Method 12 to yield N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide. To a solution of NaH (60% mineral oil—prewashed with THF) in THF at 0° C. was added N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine amide and the reaction was stirred at 0° C. for 45 minutes. Toluene-4-sulfonyl chloride was added and the reaction was stirred for 16 hours at room temperature. The reaction mixture was extracted with EtOAc (3×50 mL) and 0.2 N HCl (50 mL), and the combined organic layers were washed successively with sat. NaHCO (50 mL), and sat. NaCl (2×50 mL), dried over MgSO4, filtered, and concentrated to yield the title compound as an oil.

Workup

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. extractionThe reaction mixture was extracted with EtOAc (3×50 mL) and 0.2 N HCl (50 mL)
  3. washthe combined organic layers were washed successively with sat. NaHCO (50 mL), and sat. NaCl (2×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78baf102872f4af2b704edb7f95a2487
Source dataset
uspto-grants-2003_07
Patent number
US06586602B2

Reaction notes

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