Diisopropylethylamine → N-[2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-glycine ethyl ester

HRID 660865Notes

Reaction equation

HRID 660865 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH:19][CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4])[CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 57455730N-[2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg (0.808 mmol) of 2-bromo-1-(4-chlorophenyl)propan-1-one from Example 112A are dissolved in 1 ml acetonitrile and treated with 226 mg (1.616 mmol) of glycine ethyl ester hydrochloride and 209 mg (1.616 mmol) of N,N-diisopropylethylamine. After stirring overnight at room temperature, the reaction mixture is evaporated and the residue is partitioned between water and dichloromethane. The organic phase is separated, dried over sodium sulphate and concentrated. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1). 91 mg (42% of theory) of the target compound are thus obtained.

Workup

  1. customthe reaction mixture is evaporated
  2. customthe residue is partitioned between water and dichloromethane
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography on silica gel (eluent
  7. custom91 mg (42% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-58f14d1a8daa41fe8d904e801130b0ce
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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