Diethyl Pyrocarbonate → HCID 57847316, compound

HRID 1009957Notes

Reaction equation

HRID 1009957 reaction equation
C(O)(C(F)(F)F)=O.[S:8]1[CH:12]=[CH:11][C:10]([C@H:13]2[C@H:22]3[CH2:23][CH2:24][N:25]([C:26]([O:28]C(C)(C)C)=O)[C@H:21]3[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14]2)=[CH:9]1.[OH-].[Na+].[C:35]([NH:43][C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1C(O)=O)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O>O>[S:8]1[CH:12]=[CH:11][C:10]([C@H:13]2[C@H:22]3[CH2:23][CH2:24][N:25]([C:26]([C:45]4[CH:49]=[CH:50][CH:51]=[CH:52][C:44]=4[NH:43][C:35](=[O:42])[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[O:28])[C@H:21]3[C:20]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[NH:14]2)=[CH:9]1

Participants

8

Reactant 6

HCID 3051Diethyl PyrocarbonateHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 68482N-Benzoylanthranilic acidHCID 67150536HCID 67150536, compound

Product 1

HCID 57847316HCID 57847316, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TFA (2 ml) was added to tert-butyl (3aR*,4R*,9bR*)-4-(3-thienyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate (219 mg, 0.61 mmol), and the mixture was stirred at room temperature for 3 min. Ice was added to the reaction solution, and the mixture was basified with 8N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (3 ml), 2-(benzoylamino)benzoic acid (162 mg, 0.67 mmol) and triethylamine (124 mg, 1.2 mmol) were added. DEPC (99 mg, 0.61 mmol) was added at 0° C. and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (30 g), and eluted with hexane-ethyl acetate (9:1-3:1, v/v) to give the title compound (126 mg, 43%) as colorless crystals.

Workup

  1. additionIce was added to the reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in tetrahydrofuran (3 ml)
  7. stirringthe mixture was stirred at room temperature for 30 min
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine
  10. dry with materialdried (over anhydrous MgSO4)
  11. customthe solvent was evaporated under reduced pressure
  12. washeluted with hexane-ethyl acetate (9:1-3:1

Sources & evidence

ORD record
ord-4c4f50c79c7a4701a3c602c3b86511c2
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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