Methyl chloroformate → HCID 13319469, compound

HRID 1476005Notes

Reaction equation

HRID 1476005 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.Cl[C:18]([O:20][CH3:21])=[O:19]>C(Cl)Cl>[CH3:21][O:20][C:18]([O:1][NH:2][C:3]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:9])=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 13319469HCID 13319469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-hydroxycarbamate (1.4 g, 10.6 mmol) in DCM (10 ml) is added triethylamine (1.5 ml, 10.6 mmol) at 0° C. Methyl choroformate (814 μl, 10.6 mmol) is added drop wise. Reaction stirred for 18 hours at room temperature before being washed with water (2×10 ml), NaHCO3 (2×10 ml), dried over magnesium sulfate and concentrated in vacuo to give the title product as an oil. (1.76 g, 87%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.71 (1H, br. s.), 3.92 (3H, s), 1.50 (9H, s).

Workup

  1. customReaction
  2. washbefore being washed with water (2×10 ml), NaHCO3 (2×10 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf4015be90a1498cbfac157995bafd3a
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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