Acetic Acid → HCID 11845781, compound

HRID 1158888Notes

Reaction equation

HRID 1158888 reaction equation
[N:1]([O-])=[O:2].[Na+].C(O)(=O)C.[N+:9]([C:12]1[CH:30]=[CH:29][C:15]([CH2:16][O:17][C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH:22]([C:26]([OH:28])=[O:27])[CH2:21]2)=[O:19])=[CH:14][CH:13]=1)([O-:11])=[O:10]>O>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([N:1]=[O:2])[CH:22]([C:26]([OH:28])=[O:27])[CH2:21]2)=[O:19])=[CH:29][CH:30]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11845253HCID 11845253, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 11845781HCID 11845781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The H2O (300 mL) solution of NaNO2 (cont. 98.5%) (6.66 g) was added to the acetic acid (864 mL) solution of piperazine-1,3-dicarboxylic acid 1-(4-nitrobenzyl) ester (26.72 g) under a nitrogen atmosphere at 0° C. for 0.5 h and stirred for 1 h. In addition, the H2O (132 mL) solution of NaNO2 (cont. 98.5%) (2.41 g) was added to the solution at 0° C. for 0.5 h and stirred for 1 h. The solution was concentrated under reduced pressure and H2O (500 mL) was added to the residue. The solution was extracted with AcOEt (5 times) and organic layer was washed with brine. The mixture was dried over MgSO4, filtered and concentrated under reduced pressure to afford crude 4-nitrosopiperazine-1,3-dicarboxylic acid 1-(4-nitrobenzyl) ester as pale brown amorphous (27.83 g (gross), 25.77 g (net), 88.2%).

Workup

  1. stirringstirred for 1 h
  2. concentrationThe solution was concentrated under reduced pressure and H2O (500 mL)
  3. additionwas added to the residue
  4. extractionThe solution was extracted with AcOEt (5 times) and organic layer
  5. washwas washed with brine
  6. dry with materialThe mixture was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad5b594aeb474ec590afee5cb49eb2c3
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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