HCID 13252225, compound → HCID 13826482, compound

HRID 1906334Notes

Reaction equation

HRID 1906334 reaction equation
FC(F)(F)C([N:5]([CH2:18][P:19]([N:30]([CH3:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([N:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:22])=[S:20])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8])=O>O1CCCC1.O>[CH3:38][N:30]([P:19]([CH2:18][NH:5][CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8])([N:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:22])=[S:20])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 1

HCID 13252225HCID 13252225, compound

Product 1

HCID 13826482HCID 13826482, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-trifluoroacetyl-N-[bis(N-methyl-N-benzylamino)phosphinothioylmethyl]glycine, octyl ester (3.7 g, 6.16 mm), was dissolved in 30 ml of tetrahydrofuran containing 6 ml of water and cooled to 0° C. on an ice bath. The solution was stirred and sodium tetrahydrido boron (234 mg, 6.16 mm) was added portionwise over about 10 minutes. The solution was allowed to warm to room temperature and stirred for an additional 35 minutes. (a) 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 the 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. A thin layer chromatograph of the residue indicated that the starting material was still present. The remainder of this residue was dissolved in tetrahydrofuran (30 ml), H2O (6 ml) and sodium tetrahydridoboron (234 mg) was added with stirring. The solution was stirred for 2 hours. This solution was then treated as in step (a). The resulting residue from the repeat of step (a) was then chromatographed on silica gel employing ether to yield N-[bis(N-methyl-N-benzylamino)phosphinothioylmethyl]glycine, octyl ester (700 mg) having a refractive index ND25 =1.5404.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 35 minutes
  3. custom(a) The solvent was removed by evaporation under vacuum
  4. washthe residue was washed with water
  5. extractionthe aqueous layer and the insoluble residue were simultaneously extracted with ethyl acetate three times
  6. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe remainder of this residue was dissolved in tetrahydrofuran (30 ml)
  10. additionH2O (6 ml) and sodium tetrahydridoboron (234 mg) was added
  11. stirringwith stirring
  12. stirringThe solution was stirred for 2 hours
  13. additionThis solution was then treated as in step (a)
  14. customThe resulting residue from the repeat of step (a) was then chromatographed on silica gel

Sources & evidence

ORD record
ord-e8313f02316e4e058163280db3b0c5f7
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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