Acetic Acid → HCID 178502111, compound

HRID 449182Notes

Reaction equation

HRID 449182 reaction equation
[C:1](=[O:5])([O:3][CH3:4])[NH2:2].O=[C:7]([CH2:11][CH2:12][PH:13]([CH2:15][OH:16])=[O:14])[C:8]([OH:10])=[O:9].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:4][O:3][C:1]([NH:2]/[C:7](=[CH:11]\[CH2:12][PH:13]([CH2:15][OH:16])=[O:14])/[C:8]([OH:10])=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11722Methyl CarbamateHCID 178525999HCID 178525999, compound

Product 1

HCID 178502111HCID 178502111, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.835 g of methyl carbamate and 10.000 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 17 mL of acetic acid to be suspended. After being dissolved by heating, 68 mL of toluene was added thereto and then the solution was refluxed with vigorous stirring. The internal temperature of the reaction solution was from 106 to 108 deg. C. Four hours later, dissipation of almost all the raw materials was confirmed by HPLC measurement. At this point, the area ratio of Z form to E form was 94:6. After removing about 42 mL of the solvent under a reduced pressure, followed by adding 23 mL of acetic acid, and then the resultant was stirred for 1 hour at 80 deg. C. The precipitate which was obtained by cooling the solution gradually to room temperature and stirring over-night, was filtered and then the filtrate was washed with acetic acid. After being washed with acetone, dried for 5 hours from 40 to 50 deg. C. under a reduced pressure, 9.931 g of the objective compound was obtained (75.4% yield, Z:E=99.6:0.4).

Workup

  1. dissolutionAfter being dissolved
  2. temperatureby heating
  3. temperaturethe solution was refluxed with vigorous stirring
  4. customwas from 106 to 108 deg. C
  5. customFour hours
  6. customAfter removing about 42 mL of the solvent under a reduced pressure
  7. additionby adding 23 mL of acetic acid
  8. customThe precipitate which was obtained
  9. stirringstirring over-night
  10. filtrationwas filtered
  11. washthe filtrate was washed with acetic acid
  12. washAfter being washed with acetone
  13. customdried for 5 hours from 40 to 50 deg. C

Sources & evidence

ORD record
ord-2955b349c51449008a3478e4ee13e5a6
Source dataset
uspto-grants-2013_07
Patent number
US08481779B2

Reaction notes

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