Benzyl chloroformate → HCID 59526023, compound

HRID 385820Notes

Reaction equation

HRID 385820 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([CH2:10][NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[CH:6][CH:5]=1.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CN(C=O)C.C(OCC)(=O)C>[CH2:22]([O:21][C:19]([N:11]([CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:3])[N:9]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 59525703HCID 59525703, compound

Product 1

HCID 59526023HCID 59526023, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (88 mg, 2.20 mmol) was suspended in DMF (2.93 mL) and cooled to 0° C. Ethyl N-[(6-bromopyridin-2-yl)methyl]glycinate (200 mg, 0.73 mmol) was added and the solution was stirred for thirty minutes at 0° C. Benzyl chloroformate (0.11 mL, 0.73 mmol) was added and the solution was heated at 50° C. and allowed to stir until completion. The reaction was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. temperaturethe solution was heated at 50° C.
  2. stirringto stir until completion
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7f465d2b8e9c4fb185d4ff13ab3a3929
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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