Diethyl Pyrocarbonate → HCID 57847188, compound

HRID 735780Notes

Reaction equation

HRID 735780 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@@H:44]1[CH2:48][CH2:47][CH2:46][C@@H: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@H:45]4[CH2:46][CH2:47][CH2:48][C@H:44]4[NH:43][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:28])[C@H:21]3[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14]2)=[CH:9]1

Participants

8

Reactant 6

HCID 3051Diethyl PyrocarbonateHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67150536HCID 67150536, compoundHCID 67150718HCID 67150718, compound

Product 1

HCID 57847188HCID 57847188, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TFA (1 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 (178 mg, 0.5 mmol), and the mixture was stirred at room temperature for 3 min. Ice was added to the reaction solution, the mixture was basified with 8N aqueous sodium hydroxide solution, and the mixture was 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), and (1S,2R)-2-(benzoylamino)cyclopentanecarboxylic acid (117 mg, 0.5 mmol) and triethylamine (101 mg, 1.0 mmol) were added. DEPC (82 mg, 0.5 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 (5:1-2:1, v/v) to give the title compound (104 mg, 44%) as a colorless powder.

Workup

  1. additionIce was added to the reaction solution
  2. extractionthe mixture was extracted 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 (5:1-2:1

Sources & evidence

ORD record
ord-b275536c32fb47e38e42b032507d769c
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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