Diethyl Pyrocarbonate → HCID 57846915, compound

HRID 735756Notes

Reaction equation

HRID 735756 reaction equation
[C:1]1([C@@H:7]2[C@@H:16]3[CH2:17][CH2:18][NH:19][C@@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]1[C:35](O)=[O:36])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O.C(=O)([O-])O.[Na+]>O1CCCC1.C(#N)C>[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:35]([C@H:30]4[CH2:31][CH2:32][CH2:33][CH2:34][C@H:29]4[NH:28][C:20](=[O:27])[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:36])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 57846973HCID 57846973, compound

Product 1

HCID 57846915HCID 57846915, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3aR*,4S*,9bS)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (620 mg, 2.47 mmol), (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (671 mg, 2.7 mmol), triethylamine (0.72 ml, 5.2 mmol), acetonitrile (17 ml) and tetrahydrofuran (17 ml) was added dropwise DEPC (440 mg, 2.7 mmol) under ice-cooling, and the mixture was stirred for 10 min. The mixture was allowed to return to room temperature and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried (over anhydrous Na2 SO4), and the solvent was evaporated. The residue was subjected to column chromatography using silica gel (30 g), and eluted with hexane-ethyl acetate (9:1-7:3, v/v) to give the title compound (735 mg, 62%) as an amorphous form.

Workup

  1. temperaturecooling
  2. customto return to room temperature
  3. stirringthe mixture was stirred for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried (over anhydrous Na2 SO4)
  6. customthe solvent was evaporated
  7. washeluted with hexane-ethyl acetate (9:1-7:3

Sources & evidence

ORD record
ord-a27f8b7519c04102927ce70b765e3671
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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