HCID 13252236, compound → HCID 13826487, compound

HRID 1906339Notes

Reaction equation

HRID 1906339 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[N:15]1([P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[S:14])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

3

Reactant 1

HCID 13252236HCID 13252236, compound

Product 1

HCID 13826487HCID 13826487, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(pyrrolidino)phosphinothioylmethyl]glycine, ethyl ester (2.7 g, 0.00649 mole), was dissolved in ethanol. The solution was stirred and sodium tetrahydrido boron (245 mg, 6.49 mm) was added portionwise over a ten minute period. The solution was stirred for an additional 20 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 ether as an eluant to yield N-[bis(pyrrolidino)phosphinothioylmethyl]glycine, ethyl ester (550 mg), ND25 =1.530 and having the following analysis: Calculated: C, 48.88; H, 8.21; N, 13.16. Found: C, 48.65; H, 8.12; N, 13.04.

Workup

  1. stirringThe solution was stirred for an additional 20 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-1a9f331c12144a0d880d85923a52a73d
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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