Sodium Bicarbonate → 1236861-65-6

HRID 1772644Notes

Reaction equation

HRID 1772644 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1.C([O-])(O)=O.[Na+].C(O)(C)C.C(Cl)Cl>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:13]1[CH2:12][CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21966342Isopropanol methylene chlorideHCID 585484391,1-Dimethylethyl 3-(2-quinolinyl)-1-azetidinecarboxylate

Product 1

HCID 585484431236861-65-6

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 3-(quinolin-2-yl)azetidine-1-carboxylate (2.8 g, 9.8 mmol, as prepared above) in DCM (10 mL), TFA (10 mL) was added. The resulting mixture was stirred at rt for 2 h and concentrated to obtain a viscous oil which was dried under reduced pressure. The residue obtained was dissolved in DCM (50 mL) and stirred with saturated NaHCO3 (50 mL). The DCM layer was separated and the aqueous layer was concentrated. To the residue obtained, 20% iso-PrOH/DCM (50 mL) was added and stirred for 10 min and filtered. This procedure was repeated three times. The combined filtrates were dried over Na2SO4, filtered, and concentrated to obtain compound 24d as a gummy solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.34 (d, J=8.6 Hz, 1H), 7.94-8.01 (m, 2H), 7.76 (s, 1H), 7.59 (d, J=6.7 Hz, 1H), 7.53 (d, J=8.6 Hz, 1H), 3.89-4.30 (m, 4H), 3.72-3.82 (m, 1H).

Workup

  1. concentrationconcentrated
  2. customto obtain a viscous oil which
  3. customwas dried under reduced pressure
  4. customThe residue obtained
  5. customThe DCM layer was separated
  6. concentrationthe aqueous layer was concentrated
  7. customTo the residue obtained
  8. stirringstirred for 10 min
  9. filtrationfiltered
  10. dry with materialThe combined filtrates were dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-cb9d013db377452fac76196d10224d3a
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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