Acetic Acid → HCID 178502111, compound

HRID 449185Notes

Reaction equation

HRID 449185 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>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.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

6

Reactant 3

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

Product 1

HCID 178502111HCID 178502111, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

16.673 g of methyl carbamate, 0.549 g of p-toluenesulfonic acid monohydrate, and 20.000 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 56 mL of acetic acid to be suspended. After being dissolved by heating, 112 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. Six 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 81:19. The deposited precipitate 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, 14.966 g of the objective compound was obtained (56.8% yield, Z:E=99.7:0.3).

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. customSix hours
  6. filtrationThe deposited precipitate was filtered
  7. washthe filtrate was washed with acetic acid
  8. washAfter being washed with acetone
  9. customdried for 5 hours from 40 to 50 deg. C

Sources & evidence

ORD record
ord-aa146d15903549baaf5116f156a81c73
Source dataset
uspto-grants-2013_07
Patent number
US08481779B2

Reaction notes

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