Trifluoromethanesulfonic acid → HCID 13175234, compound

HRID 1748139Notes

Reaction equation

HRID 1748139 reaction equation
C([CH2:4][N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12]C(O)=O)[CH2:7][C:6]1=[O:16])(O)=O.FC(F)(F)S(O)(=O)=O.O1P2[O:31][P:32]3[O:34]P(O2)OP1[O:33]3.[C]=O>O>[P:32]([CH2:4][N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][P:32]([OH:31])([OH:33])=[O:34])[CH2:7][C:6]1=[O:16])([OH:34])([OH:33])=[O:31]

Participants

6

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 123290Tricyclo[3.3.1.1~3,7~]tetraphosphoxaneHCID 235108522,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acidHCID 178418416HCID 178418416, compound

Product 1

HCID 13175234HCID 13175234, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In a round-bottom flask equipped with a mechanical stirrer, a thermometer, a condenser 4.00 g (17.2 mmole) N,N′-bis(carboxymethyl)-2,5-diketopiperazine was mixed with 25 ml trifluoromethanesulfonic acid. Subsequently, the reaction mixture was heated to 75° C. and 1.89 g (8.6 mmole) tetraphosphorus hexaoxide was added slowly. Afterwards the reaction mixture was stirred for 16 hour at 75° C. During the addition and during the reaction time the evolution of carbon monoxide was observed. At ambient temperature 30 ml of water was added to the reaction mixture which subsequently was heated to 95° C. for 6 hour. A white solid precipitated that was removed by filtration at ambient temperature (yield: 4.35 g). The solid consisted of N,N′-bis(phosphonomethyl)-2,5-diketopiperazine at 98.9% by weight.

Workup

  1. customIn a round-bottom flask equipped with a mechanical stirrer
  2. additionDuring the addition
  3. temperaturesubsequently was heated to 95° C. for 6 hour
  4. customA white solid precipitated that
  5. customwas removed by filtration at ambient temperature (yield: 4.35 g)

Sources & evidence

ORD record
ord-188c8575d9d9410fbbe4cecfcf5f7c9c
Source dataset
uspto-grants-2015_10
Patent number
US09150599B2

Reaction notes

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