Trimethyl phosphite → Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

HRID 2258028Notes

Reaction equation

HRID 2258028 reaction equation
BrN1C(=O)CCC1=O.[C:9]([NH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[P:22]([O:27]C)([O:25][CH3:26])[O:23][CH3:24]>C(Cl)(Cl)(Cl)Cl>[C:12]([O:11][C:9]([NH:16][CH:17]([P:22]([O:25][CH3:26])([O:23][CH3:24])=[O:27])[C:18]([O:20][CH3:21])=[O:19])=[O:10])([CH3:14])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 8472Trimethyl phosphiteHCID 67184N-bromobutanimideHCID 637609N-Boc-glycine methyl ester

Product 1

HCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A quantity of 2.92 g (0.016 mol) of N-bromo succinimide is added to 2.82 g (0.015 mol) of N-Boc glycine, methyl ester in 230 mL of carbon tetrachloride. The mixture is heated at reflux with stirring for 1 hour, cooled to 0° C., and filtered. The filtrate is evaporated to dryness and the residue is dissolved in 30 mL of tetrahydrofuran. A quantity of 2.10 g (0.017 mol) of trimethyl phosphite is added and the solution is maintained at reflux for 18 hours. The solvent is evaporated and the product is purified by silica gel chromatography eluting with ethyl acetate; wt 2.80 g (63%);

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. dissolutionthe residue is dissolved in 30 mL of tetrahydrofuran
  6. temperaturethe solution is maintained
  7. temperatureat reflux for 18 hours
  8. customThe solvent is evaporated
  9. customthe product is purified by silica gel chromatography
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8e4c2c28646a477a9ecab200a67016eb
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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