HCID 13252235, compound → HCID 13826491, compound

HRID 1906342Notes

Reaction equation

HRID 1906342 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([N:22]([CH2:26][CH:27]=[CH2:28])[CH2:23][CH:24]=[CH2:25])([N:15]([CH2:19][CH:20]=[CH2:21])[CH2:16][CH:17]=[CH2:18])=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[CH2:26]([N:22]([P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([N:15]([CH2:19][CH:20]=[CH2:21])[CH2:16][CH:17]=[CH2:18])=[S:14])[CH2:23][CH:24]=[CH2:25])[CH:27]=[CH2:28]

Participants

3

Reactant 1

HCID 13252235HCID 13252235, compound

Product 1

HCID 13826491HCID 13826491, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(diallylamino)phosphinothioylmethyl]glycine, ethyl ester (2 g, 4.2 mm), was dissolved in ethanol (40 ml). The solution was stirred and sodium tetrahydrido boron (162 mg, 4.2 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 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(diallylamino)phosphinothioylmethyl]glycine, ethyl ester (300 mg), as a yellow solid, m.p. 80°-82° C. and having the following analysis: Calculated: C, 54.97; H, 8.14; N, 11.31. Found: C, 54.74; H, 8.13; N, 11.25.

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 resulting residue was then chromatographed on silica gel

Sources & evidence

ORD record
ord-0a9af0ea94374739a4aa92bcabd3b142
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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