4-Toluenesulfonyl chloride → HCID 66987557, compound

HRID 555787Notes

Reaction equation

HRID 555787 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[N:14]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH:15]=[N:16][C:17]=3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C1COCC1>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[N:14]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=4)[CH:15]=[N:16][C:17]=3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:9][N:10]2[S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25105771HCID 25105771, compound

Product 1

HCID 66987557HCID 66987557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50% of NaH in mineral oil (284 mg, 5.9 mmol) is added to a solution of Example 1 (1.65 g, 3.9 mmol) in THF (40 mL) at 0° C. The reaction mixture is allowed to warm to rt and stirred for 15 min. TsCl (902 mg, 4.7 mmol) is added and stirring continued for 1 h. The reaction is quenched by addition of EtOAc and H2O. The organic layer is separated, washed with brine, dried and concentrated. The crude product is purified by tituration with EtOAc/hexanes to give the title compound as a white solid. ES-MS: M+H=573.7: EtRet=5.33 min.

Workup

  1. stirringstirring
  2. waitcontinued for 1 h
  3. customThe reaction is quenched by addition of EtOAc and H2O
  4. customThe organic layer is separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product is purified by tituration with EtOAc/hexanes

Sources & evidence

ORD record
ord-c8f59ae57fa0498b9cebbbabb1a957f8
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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