Glycine methyl ester hydrochloride → HCID 19754001, compound

HRID 847545Notes

Reaction equation

HRID 847545 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C([BH3-])#N.[Na+]>CO>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:18][CH2:11][CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9]

Participants

5

Reactant 3

HCID 122755Glycine methyl ester hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamate

Product 1

HCID 19754001HCID 19754001, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-t-butoxycarbonylsarcosinal (1.50 g) and glycine methyl ester hydrochloride (1.63 g) in methanol (60 ml) was added a solution of sodium cyanoborohydride (544 mg) in methanol (10 ml) at ambient temperature. The mixture was stirred overnight at the same temperature. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml), and the solution was washed with 1 M sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (chloroform as eluent) to give N-[2-(N-t-butoxycarbonyl-N-methylamino)ethyl]glycine methyl ester (1.04 g) as an oil.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washthe solution was washed with 1 M sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (chloroform as eluent)

Sources & evidence

ORD record
ord-b3ae27468bc74f3794716925fb4a95c7
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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