Methanol → HCID 53646977, compound

HRID 1448421Notes

Reaction equation

HRID 1448421 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH2:12][P:13]([O:17]Cl)([O:15]Cl)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[CH3:21][OH:22].C(N(CC)CC)C.[CH:30]([NH2:33])([CH3:32])[CH3:31]>CCOCC>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH:12]([O:22][CH3:21])[P:13]([OH:17])([O:15][NH:33][CH:30]([CH3:32])[CH3:31])=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 6363IsopropylamineHCID 8471TriethylamineHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 53646977HCID 53646977, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (8.25 g, 0.025 mole) in 150 ml. of ether was cooled to 0° C. and treated with a solution of methanol (1.01 ml, 0.025 mole) and triethylamine (3.49 ml, 0.025 mole) in 25 ml. of ether. The solution was stirred for two hours, then filtered and the filtrate was cooled and treated with isopropylamine (4.25 ml. 0.05 mole) in 100 ml. of ether. After stirring for 16 hours, the mixture was filtered and the filtrate was washed with water, dried over sodium sulfate and concentrated in vacuo to yield ethyl N-trifluoroacetyl-N-(methoxy(isopropylamino)phosphonomethyl)glycinate (6.1 g) as a yellow oil, ND =1.4335.

Workup

  1. filtrationfiltered
  2. temperaturethe filtrate was cooled
  3. stirringAfter stirring for 16 hours
  4. filtrationthe mixture was filtered
  5. washthe filtrate was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a202be026e2c418c8f33c8a1b42cea40
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

Loading…