Hydrochloric Acid → HCID 69516762, compound

HRID 1351098Notes

Reaction equation

HRID 1351098 reaction equation
C(C1NNC(=O)C=1CC1C=CC=CC=1OCC1C=CC=CC=1C)(C)C.CC(OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH:56]([C:59]1[NH:63][N:62]=[C:61]([O:64][C@@H:65]2[O:82][C@H:81]([CH2:83][O:84]C(=O)C)[C@@H:76]([O:77]C(=O)C)[C@H:71]([O:72]C(=O)C)[C@H:66]2[O:67]C(=O)C)[C:60]=1[CH2:88][C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][C:90]=1[O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][C:98]=1[CH3:103])([CH3:58])[CH3:57].C[O-].[Na+].Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl.O.O1CCCC1.CO>[C@@H:65]1([O:64][C:61]2[C:60]([CH2:88][C:89]3[CH:94]=[CH:93][CH:92]=[CH:91][C:90]=3[O:95][CH2:96][C:97]3[CH:102]=[CH:101][CH:100]=[CH:99][C:98]=3[CH3:103])=[C:59]([CH:56]([CH3:58])[CH3:57])[NH:63][N:62]=2)[O:82][C@H:81]([CH2:83][OH:84])[C@@H:76]([OH:77])[C@H:71]([OH:72])[C@H:66]1[OH:67]

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 10942334Sodium MethoxideHCID 22932189HCID 22932189, compoundHCID 69516669HCID 69516669, compound

Product 1

HCID 69516762HCID 69516762, compound

Reagents, catalysts & solvents 5

HCID 159952Benzyltributylammonium chlorideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-isopropyl-4-[2-(2-methylbenzyloxy)-benzyl]-1,2-dihydropyrazol-3-one (68 mg), acetobromo-α-D-glucose (92 mg) and benzyl tri(n-butyl)ammonium chloride (63 mg) in dichloromethane (2 mL) was added a solution of potassium carbonate (140 mg) in water (0.5 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give a residue containing 5-isopropyl-4-[2-(2-methylbenzyloxy)benzyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole. To a solution of the residue in tetrahydrofuran (1 mL) and methanol (0.5 mL) was added sodium methoxide (28% methanol solution, 0.187 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 2 mol/L hydrochloric acid and concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (51 mg).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-b4f910c7e96140f9bce0ae3c381fdbf9
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

Loading…