Ethyl bromoacetate → N-(2,2-dimethoxyethyl)-N-(6-chloro-2-naphthalenesulfonyl)glycine ethyl ester

HRID 2086225Notes

Reaction equation

HRID 2086225 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][NH:5][S:6]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:19])[CH:15]=2)[CH:10]=1)(=[O:8])=[O:7].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C.O1CCCC1>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:20][CH3:21])[S:6]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:19])[CH:15]=2)[CH:10]=1)(=[O:8])=[O:7])[CH3:30]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 22727126N-(2,2-dimethoxyethyl)-6-chloro-2-naphthalenesulfonamide

Product 1

HCID 22727098N-(2,2-dimethoxyethyl)-N-(6-chloro-2-naphthalenesulfonyl)glycine ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(2,2-Dimethoxyethyl)-6-chloro-2-naphthalenesulfonamide was dissolved in DMF (100 ml) and combined with sodium hydride (1.16 g, in oil), cooled to 0° C., treated dropwise with a solution of ethyl bromoacetate (4.843 g) in tetrahydrofuran (15 ml) and then stirred at room temperature for 3 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, aqueous sodium bicarbonate and brine, dried and concentrated to obtain N-(2,2-dimethoxyethyl)-N-(6-chloro-2-naphthalenesulfonyl)glycine ethyl ester as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, aqueous sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e14b0866fcb4b4389a2b91efa991a48
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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