Guanidine Nitrate → HCID 86646664, compound

HRID 1799186Notes

Reaction equation

HRID 1799186 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C@@H:4]([C:7]2[CH:8]=[CH:9][C:10]([Cl:20])=[C:11]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:12]=2)[CH2:3]1.[N+:21]([O-])([OH:23])=[O:22].NC(N)=N>OS(O)(=O)=O>[O:1]=[C:2]1[NH:6][CH2:5][C@@H:4]([C:7]2[C:8]([N+:21]([O-:23])=[O:22])=[CH:9][C:10]([Cl:20])=[C:11]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])[CH:12]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 10481Guanidine NitrateHCID 86646663HCID 86646663, compound

Product 1

HCID 86646664HCID 86646664, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

N-(5-((3R)-5-Oxopyrrolidin-3-yl)-2-chlorophenyl)-2,2,2-trifluoroacetamide (7.6 g, 24.83 mmol) was dissolved in 25 mL of concentrated H2SO4 (1M solution). The mixture was then cooled to 0° C. and guanidine nitrate (24.83 mmol) was added portion-wise. The reaction mixture was stirred at 0° C. for 30 min. The mixture was then poured into a solution of ice/water. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water and brine and dried over MgSO4. The solvent was removed to give the title compound (8.7 g, 98% yield). 1H-NMR (400 MHz, CD3OD): δ 2.42-2.48 (dd, J=16.8, 6.0 Hz, 1H), 2.69-2.75 (dd, J=16.8, 8.8 Hz, 1H), 3.37-3.39 (m, 1H), 3.74-3.80 (dd, J=10.4, 8.0 Hz, 1H), 7.89 (s, 1H), 8.13 (s, 1H); MS (ESI) m/z 352.03 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-a78ac99af6594e818779d2218f7098ec
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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