Methanesulfonyl chloride → Methyl 5-methanesulfonylamino-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

HRID 1358128Notes

Reaction equation

HRID 1358128 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][CH:15]=[CH:14][C:13]=2[O:22][CH3:23])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:24][S:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][CH:15]=[CH:14][C:13]=2[O:22][CH3:23])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18188782Methyl 5-amino-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

Product 1

HCID 18189252Methyl 5-methanesulfonylamino-2-(2-methoxy-6-methoxymethoxyphenyl)-benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 32B (10 g, 34.8 mmol), in pyridine (50 mL) at room temperature was treated with methanesulfonyl chloride (2.7 mL, 34.8 mmol), stirred at room temperature for 16 hours, and concentrated. The concentrate was treated with ethyl acetate (100 mL), and the resulting solution was washed with 2N HCl, dried (Na2SO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide the desired product. MS (ESI(−)Q1MS) m/z 394 (M−H)−.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was treated with ethyl acetate (100 mL)
  3. washthe resulting solution was washed with 2N HCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-7818474b8dfd4f4fba9485b5a435cc58
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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