HCID 13252239, compound → HCID 13826488, compound

HRID 1906340Notes

Reaction equation

HRID 1906340 reaction equation
FC(F)(F)C([N:5]([CH2:12][P:13]([NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)([NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[S:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O>C(O)C>[CH:16]1([NH:15][P:13]([CH2:12][NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([NH:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[S:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 1

HCID 13252239HCID 13252239, compound

Product 1

HCID 13826488HCID 13826488, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-trifluoroacetyl-N-[bis(cyclohexylamino)phosphinothioylmethyl]glycine, ethyl ester (4 g, 8.49 mm), was dissolved in ethanol (40 ml). The solution was stirred and sodium tetrahydrido boron (322 mg, 8.49 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 residue was then chromatographed on silica gel with ether to yield N-[bis(cyclohexylamino)phosphinothioylmethyl]glycine, ethyl ester (1.3 g), m.p. 74°-90° C.

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 then chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-7c62d58d114346588ae68140198fbff2
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

Loading…