Sulfamic Acid → HCID 25164927, compound

HRID 1177976Notes

Reaction equation

HRID 1177976 reaction equation
[CH:1]([C:3]1[CH:32]=[CH:31][C:6]([C:7]([NH:9][CH2:10][C:11](=[O:30])[N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:29])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[CH2:14][CH2:13]2)=[O:8])=[CH:5][CH:4]=1)=[O:2].S(=O)(=O)([OH:35])N.Cl([O-])=O.[Na+]>CC(C)=O.O.O>[O:30]=[C:11]([N:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])[CH2:16][CH2:17]1)[CH2:10][NH:9][C:7](=[O:8])[C:6]1[CH:31]=[CH:32][C:3]([C:1]([OH:35])=[O:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 57855675HCID 57855675, compound

Product 1

HCID 25164927HCID 25164927, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

4-Formyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (40 mg, 0.90 mmol) was dissolved in an acetone-water mixture (1:1, 0.9 mL) and cooled to 0° C. A mixture of sulphamic acid (26 mg, 0.27 mmol) and sodium chlorite (32 mg, 0.36 mmol) dissolved in minimum amount of water was then added. The resulting mixture was allowed to warm to room temperature and stirred for 30 minutes. 5 mL of water was then added, and the product was extracted with ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulphate and concentrated to afford 25 mg (61% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-terephthalamic acid. LCMS Purity: 95.8%, 1H NMR (DMSO-d6): δ 13 (bs, 1H). 8.8 (m, 1H), 8.1-7.9 (m, 4H), 7.9-7.8 (m, 1H), 7.8-7.7 (m, 1H), 7.7 (m, 1H), 7.6-7.5 (m, 1H), 4.3-4.1 (m, 4H), 3.6-3.4 (m, 8H).

Workup

  1. additionwas then added
  2. temperatureto warm to room temperature
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b63e4c44be8542be8ebd5ff6f1b2c3bd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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