Hydrochloric Acid → HCID 56837183, compound

HRID 1038301Notes

Reaction equation

HRID 1038301 reaction equation
[CH2:1]([O:3][C@@H:4]1[C@@H:9]([O:10][CH3:11])[C@H:8]([CH3:12])[O:7][C@@H:6]([O:13][N:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])=[CH:29][CH:28]=4)[N:23]=3)=[CH:18][CH:17]=2)[C@@H:5]1[O:41][CH3:42])[CH3:2].C(O)C.Cl.C(=O)(O)[O-].[Na+]>C(O)C.O>[CH2:1]([O:3][C@@H:4]1[C@@H:9]([O:10][CH3:11])[C@H:8]([CH3:12])[O:7][C@@H:6]([O:13][NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:40])([F:39])[C:35]([F:37])([F:38])[F:36])=[CH:29][CH:28]=4)[N:23]=3)=[CH:20][CH:21]=2)[C@@H:5]1[O:41][CH3:42])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 866626846-Deoxy-3-O-ethyl-2,4-di-O-methyl-1-O-[(4-{1-[4-(pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl}benzylidene)amino]-α-L-mannopyranose

Product 1

HCID 56837183HCID 56837183, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of 4-[1-(4-pentafluoroethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzaldehyde O-((2S,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyl-tetrahydropyran-2-yl)-oxime (P-1; 257 milligrams (mg), 0.429 millimoles (mmol)) in 190 proof ethyl alcohol (EtOH; 10 milliliters (mL)) at room temperature was added pyridine borane complex (200 microliters (μL), 1.99 mmol) in one portion. 3 N Hydrochloric acid (HCl; 1.4 mL) was then added dropwise. When the addition was complete, the mixture stirred at room temperature for 23 hours (h). The mixture was then diluted with EtOH/water (H2O) and treated with saturated sodium bicarbonate (NaHCO3). The resulting aqueous mixture was extracted with ethyl acetate (EtOAc; 2×). The organic extracts were combined, dried, washed with brine and dried with anhydrous sodium sulfate (Na2SO4). The solvent was evaporated at room temperature under vacuum. The resulting crude material was purified by silica gel chromatography (eluting with 50% EtOAc in Hexane). The title product (164 mg, 63%) was isolated as a white sticky solid: 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.22-8.16 (m, 2H), 7.87-7.80 (m, 2H), 7.50 (d, J=8.2 Hz, 2H), 7.46-7.38 (m, 2H), 6.04 (s, 1H), 5.01 (d, J=1.4 Hz, 1H), 4.18 (s, 2H), 3.84-3.28 (m, 12H), 3.11 (dd, J=12.0, 6.5 Hz, 1H), 1.30 (ddd, J=20.9, 10.3, 4.6 Hz, 6H); ESIMS m/z 603 (M+H).

Workup

  1. additionWhen the addition
  2. extractionThe resulting aqueous mixture was extracted with ethyl acetate (EtOAc; 2×)
  3. customdried
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate (Na2SO4)
  6. customThe solvent was evaporated at room temperature under vacuum
  7. customThe resulting crude material was purified by silica gel chromatography (eluting with 50% EtOAc in Hexane)

Sources & evidence

ORD record
ord-b7f0698470c24fe8819065848a90b29b
Source dataset
uspto-grants-2013_10
Patent number
US08551914B2

Reaction notes

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