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

HRID 1699089Notes

Reaction equation

HRID 1699089 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-4cc472a0d943477f8c9217bb5d39e83d
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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