4-Toluenesulfonyl chloride → HCID 86593169, compound

HRID 459934Notes

Reaction equation

HRID 459934 reaction equation
CC1C=CC(S(Cl)(=O)=[O:9])=CC=1.[Cl:12][C:13]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:14]=1[CH2:15][N:16]([CH3:35])[C:17]([N:19]1[CH2:24][CH2:23]/[C:22](=[N:25]/O)/[CH2:21][C@@H:20]1C1C=CC(F)=CC=1C)=[O:18]>CC(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:12][C:13]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:14]=1[CH2:15][N:16]([CH3:35])[C:17]([N:19]1[CH2:24][CH2:23][C:22](=[O:9])[NH:25][CH2:21][CH2:20]1)=[O:18]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178427849HCID 178427849, compound

Product 1

HCID 86593169HCID 86593169, compoundYield 117.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

A solution of p-tosyl chloride (28 mg) in acetone (0.5 mL) was added drop-wise to a mixture of intermediate 25b (43 mg) in acetone (1 mL) and 5% sodium carbonate solution (1 mL) under a Nitrogen atmosphere. The mixture was stirred at room temperature for 15 minutes, then it was heated to reflux for 45 minutes. The mixture was allowed to cool to r.t., and the aqueous residue was extracted with DCM. The organic layer was washed with a 5% sodium hydrogen carbonate solution (10 mL). The aqueous phase was re-extracted with DCM (3×20 mL). The combined organic extracts were dried and concentrated in vacuo to give the crude 7-(R)-4-fluoro-2-methyl-phenyl)-5-oxo-[1,4]-diazepane-1-carboxylic acid, (2,5-dichloro-benzyl)-methylamide (38 mg).

Workup

  1. temperatureit was heated
  2. temperatureto reflux for 45 minutes
  3. temperatureto cool to r.t.
  4. extractionthe aqueous residue was extracted with DCM
  5. washThe organic layer was washed with a 5% sodium hydrogen carbonate solution (10 mL)
  6. extractionThe aqueous phase was re-extracted with DCM (3×20 mL)
  7. customThe combined organic extracts were dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f864cde2cc043adbd3d344d7e240dfb
Source dataset
uspto-grants-2007_03
Patent number
US07196077B2

Reaction notes

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