HCID 13252237, compound → HCID 13826486, compound

HRID 1906338Notes

Reaction equation

HRID 1906338 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([NH:18][CH2:19][CH3:20])([NH:15][CH2:16][CH3:17])=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[CH2:16]([NH:15][P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([NH:18][CH2:19][CH3:20])=[S:14])[CH3:17]

Participants

3

Reactant 1

HCID 13252237HCID 13252237, compound

Product 1

HCID 13826486HCID 13826486, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(ethylamino)phosphinothioylmethyl]glycine, ethyl ester (2 g, 0.0055 mole), was dissolved in ethanol. The solution was stirred and sodium tetrahydrido boron (210 mg, 0.0055 mole) was added portionwise over a ten minute period. The solution was stirred for an additional 40 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 employing dichloromethane and then ether to yield N-[bis(ethylamino)phosphinothioylmethyl]glycine, ethyl ester (300 mg), ND25 =1.5128 and having the following analysis: Calculated: C, 40.44; H, 8.30; N, 15.72; P, 11.59; S, 11.99. Found: C, 40.19; H, 8.06; N, 15.37; P, 11.33; S, 11.74.

Workup

  1. stirringThe solution was stirred for an additional 40 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

Sources & evidence

ORD record
ord-8a92f17e78204a3aa5bc4b05c6b46190
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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