Hydrochloric Acid → HCID 82415197, compound

HRID 1751979Notes

Reaction equation

HRID 1751979 reaction equation
C[C:2]1(C)[CH2:10][C:9]2[NH:8][C:7]([CH:11]=[O:12])=[CH:6][C:5]=2[C:4](=[O:13])[CH2:3]1.C1(=O)CCCC(=O)C1.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N.Cl.C(=O)([O-])[O-].[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+].C(=O)(O)[O-].[Na+]>O>[O:13]=[C:4]1[CH2:3][CH2:2][CH2:10][C:9]2[NH:8][C:7]([CH:11]=[O:12])=[CH:6][C:5]1=2

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 104341,3-CyclohexanedioneHCID 439213D-GlucosamineHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 85611552HCID 85611552, compound

Product 1

HCID 82415197HCID 82415197, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By using a procedure analogous to preparation of 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxaldehyde, 1,3-cyclohexane dione 4.55 g (39.36 mmol) was condensed with D-glucosamine.HCl 6.84 g (31.72 mmol) in water 40 mL in the presence of sodium carbonate 1.683 g, at ambient temperature for 11 days. (The polyol intermediate did not crystallize). The reaction mixture was extracted twice with chloroform (2×100 mL) and the aqueous phase was retained. The organic phases were back-extracted with water 150 mL. The combined aqueous phases were cooled in a 1 L flask on ice, solid sodium periodate 35.0 g (160 mmol) was gradually added over 10 minutes and the reaction was continued for additional 20 minutes on ice. The mixture was them made basic by gradual addition of saturated sodium bicarbonate solution 80 mL (foaming) and the stirring was continued for 30 minutes. The reaction mixture was filtered, the solids were washed with chloroform 0.5 L. The biphasic filtrates were shaken and separated, the aqueous phase was re-extracted with additional chloroform 0.5 L. The combined organic extracts were dried (MgSO4) and evaporated. The obtained crystalline residue was suspended in benzene (10 mL), collected by filtration, washed with benzene and dried. Y=534 mg (10% overall) of a pale yellow solid. 1H-NMR (d6-DMSO, 400 MHz): 12.50 (br s, 1H), 9.51 (s, 1H), 7.23 (d, 2.0 Hz, 1H), 2.81 (t, 6.3 Hz, 2H), 2.39 (dd, 6.8 Hz, 5.8 Hz, 2H), 2.03 (quint, 6.2 Hz, 2H)

Workup

  1. custom(The polyol intermediate did not crystallize)
  2. extractionThe reaction mixture was extracted twice with chloroform (2×100 mL)
  3. extractionThe organic phases were back-extracted with water 150 mL
  4. additionwas gradually added over 10 minutes
  5. waitthe stirring was continued for 30 minutes
  6. filtrationThe reaction mixture was filtered
  7. washthe solids were washed with chloroform 0.5 L
  8. customseparated
  9. extractionthe aqueous phase was re-extracted with additional chloroform 0.5 L
  10. dry with materialThe combined organic extracts were dried (MgSO4)
  11. customevaporated
  12. filtrationcollected by filtration
  13. washwashed with benzene
  14. customdried

Sources & evidence

ORD record
ord-7c8752f543644078b8a9974d57b94ab8
Source dataset
uspto-grants-2015_10
Patent number
US09162981B2

Reaction notes

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