Isopropanol → HCID 131715072, compound

HRID 1906335Notes

Reaction equation

HRID 1906335 reaction equation
FC(F)(F)C([N:5]([CH2:11][P:12]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[S:13])[CH2:6][C:7]([O:9]C)=O)=O.[CH:28]([OH:31])([CH3:30])[CH3:29]>>[O:23]1[CH2:22][CH2:21][N:20]([P:12]([CH2:11][NH:5][CH2:6][C:7]([O:31][CH:28]([CH3:30])[CH3:29])=[O:9])([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[S:13])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 3776IsopropanolHCID 13252226HCID 13252226, compound

Product 1

HCID 131715072HCID 131715072, compound

Conditions

Temperature
0 °C

Procedure

N-trifluoroacetyl-N-[bis(morpholino)phosphinothioylmethyl]glycine, methyl ester (5.35 g, 0.0123 mole) was dissolved in isopropanol and cooled to 0° C. on an ice bath. The solution was stirred and sodium tetrahydrido boron (467 mg, 0.0123 mole) was added portionwise over a ten minute period. The solution was allowed to warm to room temperature and stirred for an additional 45 minutes. The solvent was removed by evaporation under vacuum and the resulting 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 25% ethanol in ethyl acetate (V:V) to obtain N-[bis(morpholino)phosphinothioylmethyl]glycine, isopropyl ester (300 mg), having a refractive index ND25 =1.5205 and the following analysis: Calculated: C, 44.33; H, 7.78; N, 11.08. Found: C, 44.83; H, 7.59; N, 10.76.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 45 minutes
  3. customThe solvent was removed by evaporation under vacuum
  4. washthe resulting residue was washed with water
  5. extractionthe aqueous layer and 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. customThe resulting residue was then chromatographed on silica gel employing 25% ethanol in ethyl acetate (V:V)

Sources & evidence

ORD record
ord-143bd0053b9e40eb880a5cbe21f565ca
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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