Triethylamine → HCID 86654181, compound

HRID 1476006Notes

Reaction equation

HRID 1476006 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][CH2:21][CH2:22][O:23][CH3:24])=[O:19]>C(Cl)Cl>[C:5]([O:4][C:3]([NH:2][O:1][C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[O:19])=[O:9])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694002-Methoxyethyl chloroformateHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 86654181HCID 86654181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-hydroxycarbamate (1.5 g, 11.3 mmol) in DCM (50 ml) is added triethylamine (1.6 ml, 11.3 mmol) at 0° C. Chloro(2-methoxyethoxy)methanone (1.56 g, 11.3 mmol) is added dropwise. Reaction is stirred for 18 hours at room temperature before being washed with water (2×10 ml), NaHCO3 (2×10 ml), dried (MgSO4) and concentrated in vacuo to give the title product as an oil. (0.67 g, 25%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.74-8.46 (1H, m), 4.23-4.73 (2H, m), 3.45-3.84 (2H, m), 3.34 (3H, s), 1.41 (9H, s).

Workup

  1. customReaction
  2. washbefore being washed with water (2×10 ml), NaHCO3 (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-147362d40f2e4831b93d71e7bbffebda
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

Loading…