HCID 13252238, compound → HCID 13826489, compound

HRID 1906341Notes

Reaction equation

HRID 1906341 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([NH:19][CH:20]([CH3:22])[CH3:21])([NH:15][CH:16]([CH3:18])[CH3:17])=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[CH:20]([NH:19][P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([NH:15][CH:16]([CH3:18])[CH3:17])=[S:14])([CH3:21])[CH3:22]

Participants

3

Reactant 1

HCID 13252238HCID 13252238, compound

Product 1

HCID 13826489HCID 13826489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(isopropylamino)phosphinothioylmethyl]glycine, ethyl ester (2 g, 5.1 mm), was dissolved in ethanol. The solution was stirred and sodium tetrahydrido boron (194 mg, 5.1 mm) was added portionwise over a ten minute period. The solution was stirred for an additional 30 minutes. The solvent was removed by evaporation under vacuum and the residue was washed with water. The water was 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 residue was chromatographed on silica gel employing ether as an eluant to yield N-[bis(isopropylamino)phosphinothioylmethyl]glycine, ethyl ester, as a white solid, m.p. 63° C. and having the following analysis: Calculated: C, 42.17; H, 8.90; N, 13.40; P, 9.90; S, 10.20. Found: C, 41.98; H, 8.10; N, 13.22; P, 9.39; S, 9.74.

Workup

  1. stirringThe solution was stirred for an additional 30 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 residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-5a9c6dc040d04e4a83d0c6ffa12efce2
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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