Calcium Carbonate → HCID 58975517, compound

HRID 1178783Notes

Reaction equation

HRID 1178783 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Ca+2].[Br-:25].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.OS([O-])=O.[Na+]>CO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:25])[CH:15]=2)[NH:10][C:9]1=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10112Calcium CarbonateHCID 23665763Sodium BisulfiteHCID 53442637BenzyltrimethylammoniumtribromideHCID 57049298tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbamate2×

Product 1

HCID 58975517HCID 58975517, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound, which was isolated as a side-product of the preparation of 6A, may also be prepared from 8A as follows: To a solution of 8A (750 mg, 2.42 mmol) in MeOH (12 mL) and CH2Cl2 (12 mL) stirring at RT under argon was added CaCO3 (484 mg, 4.83 mmol) and benzyltrimethylammonium tribromide (1885 mg, 4.83 mmol). After 18 h 10% aqueous NaHSO3 (5 mL) was added to the reaction mixture, and stirring was continued for 30 min. Partial evaporation under vacuum was performed to remove nearly all of the organic solvents before the mixture was extracted twice with CH2Cl2. The combined extracts were washed with water, dried (MgSO4), and evaporated under vacuum. The resulting residue was chromatographed on silica gel eluted with 25% Et2O in CH2Cl2 to obtain the title compound (746 mg) as a white foam.

Workup

  1. customPartial evaporation under vacuum
  2. customto remove nearly all of the organic solvents before the mixture
  3. extractionwas extracted twice with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated under vacuum
  7. customThe resulting residue was chromatographed on silica gel
  8. washeluted with 25% Et2O in CH2Cl2

Sources & evidence

ORD record
ord-4f9660bbf0984e2c853c5b203c39e8ef
Source dataset
uspto-grants-2007_10
Patent number
US07276608B2

Reaction notes

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