Ethanol → HCID 20827833, compound

HRID 1917510Notes

Reaction equation

HRID 1917510 reaction equation
[C:1]([O:5][C:6]([NH:8][O:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][N:15]1CCOCC1.ClC(OCC(C)C)=O.CN.C(O)C>C1COCC1>[CH3:14][NH:15][C:11](=[O:13])[CH2:10][O:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 702EthanolHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2755974(Boc-aminooxy)acetic acid

Product 1

HCID 20827833HCID 20827833, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(tert-butoxycarbonylaminooxy)acetic acid (87a, 1 g, 5.23 mmol) in anhydrous THF was chilled in an ice bath and N-methylmorpholine (863 μL, 7.85 mmol) and isobutyl chloroformate (746 μL, 5.75 mmol) were added sequentially. The mixture was stirred under an N2 atmosphere for 20 min. A 33 wt % solution of methanamine in ethanol (1.3 mL, 10.46 mmol) was added to the reaction which was subsequently allowed to warm to room temperature with stirring overnight. The THF was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was washed with H2O×2 and dried over anhydrous Na2SO4. The ethyl acetate was removed in vacuo to yield tert-butyl 2-(methylamino)-2-oxoethoxycarbamate (87b, 775 mg, 3.80 mmol).

Workup

  1. stirringwith stirring overnight
  2. customThe THF was removed in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with H2O×2
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe ethyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-55436ff8f50a4ac59643a1e425ac3a7e
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

Loading…