N,O-Dimethylhydroxylamine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 2037733Notes

Reaction equation

HRID 2037733 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.[CH3:25][NH:26][O:27][CH3:28]>O1CCCC1>[CH3:28][O:27][N:26]([CH3:25])[C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)acetic acid (8.75 g, 0.05 mol) in tetrahydrofuran (150 mL) was added CDI (11.34 g, 0.07 mmol) at 0° C. The formed mixture was stirred for 1 h. Then N,O-dimethylhydroxylamine (6.8 g, 0.07 mol) and TEA (8 mL) were added to the above mixture. The mixture was stirred at rt overnight. When the reaction was over, the mixture was concentrated. The residue was washed with 1 N aq HCl and aq. NaHCO3 (3×). The combined organic phase was concentrated to give crude product, which was used for next step without purification. 1H NMR (400 MHz, CDCl3): δ=1.42 (s, 9H), 3.16 (s, 3H), 3.66 (s, 3H), 4.04 (s, 2H), 5.22 (s, 1H).

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationwas concentrated
  3. washThe residue was washed with 1 N aq HCl and aq. NaHCO3 (3×)
  4. concentrationThe combined organic phase was concentrated
  5. customto give crude product, which
  6. customwas used for next step without purification

Sources & evidence

ORD record
ord-3b81861b73df4c1bbd2005cf00aabaa9
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…