Triethylamine → 2-Acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester

HRID 1157446Notes

Reaction equation

HRID 1157446 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][S:21]([CH3:20])(=[O:23])=[O:22])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 685215492-Acetylamino-5-(3-hydroxypropoxy)benzoic acid methyl ester

Product 1

HCID 866229032-Acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-acetylamino-5-(3-hydroxypropoxy)benzoic acid methyl ester (689 mg, 2.6 mmol) in dichloromethane (25 mL) cooled to 0° C. were added methanesulfonyl chloride (1 mL, 12.9 mmol) and triethylamine (3.6 mL, 25.8 mmol). The mixture was warmed to room temperature and stirred for 2.5 h. The mixture was diluted with ethyl acetate (100 mL) and washed with 1 N HCl (aq.) (1×50 mL), sat. NaHCO3 (aq.) (1×50 mL) and brine (1×50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Crude 2-acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester thus obtained was used without further purification in the next step.

Workup

  1. washwashed with 1 N HCl (aq.) (1×50 mL), sat. NaHCO3 (aq.) (1×50 mL) and brine (1×50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a18c6b5825c4fe08ce63b558d4ce838
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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