Methane → HCID 10465678, compound

HRID 1612774Notes

Reaction equation

HRID 1612774 reaction equation
C(OC([NH:8][CH2:9][C:10]([OH:20])([CH3:19])[CH2:11][P:12]([CH2:15][CH2:16][CH2:17][CH3:18])(=[O:14])[O-:13])=O)(C)(C)C.[Na+].C(O)CC.C.C1OC1C>Cl.C(O)C>[NH2:8][CH2:9][C:10]([OH:20])([CH3:19])[CH2:11][P:12]([CH2:15][CH2:16][CH2:17][CH3:18])(=[O:13])[OH:14]

Participants

7

Reactant 4

HCID 297MethaneHCID 10311-PropanolHCID 6378Propylene OxideHCID 86746591HCID 86746591, compound

Product 1

HCID 10465678HCID 10465678, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 0.73 g of sodium 3-(N-tert.-butoxycarbonylamino)-2-hydroxy-2-methyl-propyl(n-butyl)phosphinate is dissolved in 10 ml of 1.0 aqueous hydrochloric acid and the solution stirred at 20° for 16-20 hours. After this time the solution is washed with dichloromethane followed by ether and the water removed under reduced pressure at 40° to afford an oily solid. This solid is treated with n-propanol and a few grams of charcoal. Subsequent heating to reflux and filtration gives a colourless solution. Removal of the solvent in vacuo and drying of the solid in vacuo at 80° gives a pale yellow solid. Dissolution of this solid in absolute ethanol followed by treatment with propylene oxide affords a white solid. Recrystallisation from an ethanol/acetone mixture gives 3-amino-2-hydroxy-2-methyl-propyl(n-butyl)phosphinic acid of m.p. 187°-189°.

Workup

  1. washAfter this time the solution is washed with dichloromethane
  2. customthe water removed under reduced pressure at 40°
  3. customto afford an oily solid
  4. temperatureSubsequent heating
  5. temperatureto reflux
  6. filtrationfiltration
  7. customgives a colourless solution
  8. customRemoval of the solvent in vacuo
  9. customdrying of the solid in vacuo at 80°
  10. customgives a pale yellow solid
  11. customaffords a white solid
  12. customRecrystallisation from an ethanol/acetone mixture

Sources & evidence

ORD record
ord-8b698a7686534926a47e2a2e5c0bda23
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

Loading…