Ethyl bromoacetate → N-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

HRID 1794933Notes

Reaction equation

HRID 1794933 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10].C(N(CC)CC)C.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>ClCCl>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][NH:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH3:34]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 22222392n-(2-Aminoethyl)-2-nitro-benzenesulfonamide acetic acid salt

Product 1

HCID 22222417N-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-glycine ethyl esterYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-aminoethyl)-2-nitro-benzenesulfonamide acetic acid salt (15.15 g, 49.6 mmol) and triethylamine (15.16 g, 0.15 mol) in dichloromethane (100 mL) was added ethyl bromoacetate (16.7 g 0.100 mol) with stirring at room temperature. After additional stirring for 1 h, the reaction mixture was washed with brine (100 mL). The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo and the residue was triturated in ethyl ether (100 mL) to afford the titled compound as a white solid (8.1 g, 49%). 1H-NMR (500 MHz; DMSO-d6) δ 8.02˜7.96 (m, 2H), 7.87˜7.84 (m, 2H), 4.05 (q, 2H), 3.23 (s, 2H), 2.95 (t, 2H), 2.57 (t, 2H) 1.16 (t, 3H).

Workup

  1. stirringAfter additional stirring for 1 h
  2. washthe reaction mixture was washed with brine (100 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was triturated in ethyl ether (100 mL)

Sources & evidence

ORD record
ord-c793152ce022484c9120eb30b27b747c
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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