Methyl Benzoate → 3-(2-Methanesulfonylamino-ethyl)-benzoic Acid Methyl Ester

HRID 480332Notes

Reaction equation

HRID 480332 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][NH2:12])[CH:5]=1.COC(=O)C1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][NH:12][S:25]([CH3:24])(=[O:27])=[O:26])[CH:5]=1

Participants

6

Reactant 4

HCID 7150Methyl BenzoateHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10511548Methyl 3-(2-aminoethyl)benzoate

Product 1

HCID 541373593-(2-Methanesulfonylamino-ethyl)-benzoic Acid Methyl EsterYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(2-amino-ethyl)-benzoic acid methyl ester (500 mg) in CH2Cl2 (35 mL) at 0° C. was added amino-ethyl)-benzoic acid methyl ester (500 mg) in CH2Cl2 (35 mL) at 0° C. was added methanesulfonyl chloride (292 mg, 2.55 mmol) and triethylamine (1.6 mL, 11.5 mmol). The reaction was stirred at room temperature for 18 h and was washed consecutively with 5.5% HCl, water, saturated NaHCO3, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to yield the title compound (522 mg) as a white solid. MS 275 (M+18).

Workup

  1. washwas washed consecutively with 5.5% HCl, water, saturated NaHCO3, and brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4f4acb288c0243a18dc2c1b04c397f94
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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