Hydrochloric Acid → HCID 58292665, compound

HRID 1798075Notes

Reaction equation

HRID 1798075 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:15][B:14]([OH:24])[C:13]=2[CH:12]=[C:11]([O:25]C2CCCCO2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCN(CC)CC>C1COCC1>[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:15][B:14]([OH:24])[C:13]=2[CH:12]=[C:11]([OH:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 58292869HCID 58292869, compound

Product 1

HCID 58292665HCID 58292665, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 2-(4-(benzyloxy)-1-hydroxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.48 g, 3.1 mmol) in THF (10 mL) was slowly added conc. HCl (1.48 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h and neutralized by addition of Et3N. The resulting mixture was extracted with EtOAc (3×25 mL), dried over anhydrous Na2SO4 and concentrated to give the title compound as a white powder (1.01 g, Yield: 95%).

Workup

  1. customat 0° C
  2. extractionThe resulting mixture was extracted with EtOAc (3×25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2691941c7fba4962a254af48c6bd61d2
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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