HCID 131715073, compound → HCID 13826484, compound

HRID 1906336Notes

Reaction equation

HRID 1906336 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([N:18]([CH3:20])[CH3:19])([N:15]([CH3:17])[CH3:16])=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[CH3:20][N:18]([P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([N:15]([CH3:16])[CH3:17])=[S:14])[CH3:19]

Participants

3

Reactant 1

HCID 131715073HCID 131715073, compound

Product 1

HCID 13826484HCID 13826484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(dimethylamino)phosphinothioylmethyl]glycine, ethyl ester (1 g, 0.00275 mole), was dissolved in ethanol (20 ml). The resulting solution was stirred and sodium tetrahydrido boron (0.104 g, 0.00275 mole) was added portionwise over a ten minute period. The resulting solution was stirred for 60 minutes. The solvent was removed by evaporation under vacuum and the residue was washed with water. The water washings were saturated with sodium chloride and the aqueous layer and insoluble residue were simultaneously extracted with ethyl acetate three times. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was then chromatographed on silica gel with ether to yield N-[bis(dimethylamino)phosphinothioylmethyl]glycine, ethyl ester, ND25 =1.5317.

Workup

  1. stirringThe resulting solution was stirred for 60 minutes
  2. customThe solvent was removed by evaporation under vacuum
  3. washthe residue was washed with water
  4. extractionthe aqueous layer and insoluble residue were simultaneously extracted with ethyl acetate three times
  5. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was then chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-c01708afe90444d3872c169b5846a941
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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