Calcium Carbonate → HCID 58975517, compound

HRID 1643871Notes

Reaction equation

HRID 1643871 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]carbamate

Product 1

HCID 58975517HCID 58975517, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 87D (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 (1.885 g, 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. waitwas continued for 30 min
  2. customPartial evaporation under vacuum
  3. customto remove nearly all of the organic solvents before the mixture
  4. extractionwas extracted twice with CH2Cl2
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum
  8. customThe resulting residue was chromatographed on silica gel
  9. washeluted with 25% Et2O in CH2Cl2

Sources & evidence

ORD record
ord-15301b58f33843ba9dcd54f09dc0a339
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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