Dichloromethane → N,N-bis-(2-methylthioethyl)-glycine methyl ester

HRID 2296589Notes

Reaction equation

HRID 2296589 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][CH3:9].C(N(C(C)C)CC)(C)C.[CH3:19][O:20][C:21](=[O:24])[CH2:22]Br.C(Cl)Cl>C(#N)C>[CH3:19][O:20][C:21](=[O:24])[CH2:22][N:5]([CH2:6][CH2:7][S:8][CH3:9])[CH2:4][CH2:3][S:2][CH3:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 15410127Bis-(2-methylthioethyl)-amine

Product 1

HCID 18387082N,N-bis-(2-methylthioethyl)-glycine methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

165 mg of bis-(2-methylthioethyl)-amine (Example 8b) is dissolved in 20 ml of acetonitrile and mixed with 174 μl of diisopropylethylamine. 92.7 μl of bromoacetic acid methyl ester, dissolved in 20 ml of acetonitrile, is added in drops under a cover-gas atmosphere, and the batch is stirred for 18 hours at room temperature. The acetonitrile is drawn off, the residue is taken up with methylene chloride and washed twice with saturated sodium bicarbonate solution. The organic phase is dried with sodium sulfate and concentrated by evaporation, and the residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol: Yield 183 mg=77% of theory.

Workup

  1. additionis added in drops under a cover-gas atmosphere
  2. washwashed twice with saturated sodium bicarbonate solution
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is purified by chromatography with the mobile solvent system of methylene chloride/methanol

Sources & evidence

ORD record
ord-b97275aca5914982822d5965746a0bd5
Source dataset
uspto-grants-2002_12
Patent number
US06488909B1

Reaction notes

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