Triethylamine → [3-(2-Methanesulfonylamino-ethyl)-phenyl]-acetic acid tert-butyl ester

HRID 890824Notes

Reaction equation

HRID 890824 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1CCN)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([N:20](CC)CC)[CH3:19].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH2:19][CH2:18][NH:20][S:26]([CH3:25])(=[O:28])=[O:27])[CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54411372[2-(2-Amino-ethyl)-phenyl]-acetic acid tert-butyl ester

Product 1

HCID 54170234[3-(2-Methanesulfonylamino-ethyl)-phenyl]-acetic acid tert-butyl esterYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [2-(2-amino-ethyl)-phenyl]-acetic acid tert-butyl ester (422.5 mg, 1.795 mmol), triethylamine (908 mg, 8.977 mmol), and methanesulfonyl chloride (226.2 mg, 1.975 mmol) in CH2Cl2 (20 mL) was combined and stirred at 0° C. for 18 h. The organic solution was washed consecutively with dilute HCl, water, saturated NaHCO3, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to provide the title sulfonamide (535 mg). MS 331 (M+18).

Workup

  1. washThe organic solution was washed consecutively with dilute 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-cfddd78a754d4107b180ff0de189840e
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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