Glycine methyl ester hydrochloride → HCID 19754001, compound

HRID 1588806Notes

Reaction equation

HRID 1588806 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 1M 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 1M 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-6df856dfca404196aff5735464a014eb
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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