Ethyl Acetate → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 530449Notes

Reaction equation

HRID 530449 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:26][NH:27][O:28][CH3:29].CCOC(C)=O>C(Cl)Cl>[CH3:29][O:28][N:27]([CH3:26])[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{[(tert-Butoxy)carbonyl]amino}acetic acid (5.00 g, 28.5 mmol) was dissolved in DCM (50 mL), CDI (5.09 g, 31.4 mmol) was added and the reaction mixture was stirred for 1 h. N,O-dimethylhydroxylamine hydrochloride (3.06 g, 31.4 mmol) was added and the reaction mixture was stirred for 16 h. EtOAc (150 mL) was added and the reaction mixture was washed with 1 M aq HCl (50 mL), sat aq NaHCO3 (2×50 mL), dried (Na2SO4) and concentrated in vacuo to give the crude title compound (5.13 g, 82%) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred for 16 h
  2. washthe reaction mixture was washed with 1 M aq HCl (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83b0e6e2ac454b92afabccc4c0ade2df
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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