Acetic Acid → HCID 178502111, compound

HRID 449184Notes

Reaction equation

HRID 449184 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 71.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

67.56 g of methyl carbamate, 2.97 g of p-toluenesulfonic acid monohydrate and 108.06 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 160 mL of acetic acid to be suspended. After being dissolved by heating, 800 mL of toluene was added thereto and then the solution was refluxed with vigorous stirring. According to the same procedure as Example 1, 102.28 g of the objective compound was obtained (71.9% yield, Z:E=99.8:0.2).

Workup

  1. dissolutionAfter being dissolved
  2. temperatureby heating
  3. temperaturethe solution was refluxed with vigorous stirring

Sources & evidence

ORD record
ord-1de4fdd9eafd4a31850d4001408ac03a
Source dataset
uspto-grants-2013_07
Patent number
US08481779B2

Reaction notes

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