Hydrochloric Acid → HCID 58292665, compound

HRID 1798264Notes

Reaction equation

HRID 1798264 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:24]C3CCCCO3)[CH:14]=[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]1=2)[CH3:2].Cl>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:24])[CH:14]=[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58292869HCID 58292869, compound

Product 1

HCID 58292665HCID 58292665, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-benzyloxy-1-hydroxy-6-(tetrahydro-pyran-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.00 g, 2.35 mmol) in THF (10 mL) was treated with 6N HCl (0.3 mL) at 0° C. for 2 h. The mixture was diluted with ethyl acetate and washed with brine. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:3) to afford the title compound (710 mg, 89%). 1H NMR (300 MHz, CD3OD) δ 7.51-7.38 (m, 5H), 6.64 (s, 1H), 6.61 (s, 1H), 5.58-5.53 (m, 1H), 5.14 (s, 2H), 4.12 (q, 2H), 3.28-3.20 (m, 1H), 2.47-2.43 (m, 1H), 1.22 (t, 3H).

Workup

  1. washwashed with brine
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:3)

Sources & evidence

ORD record
ord-5ae2e59a486843c8b2cff294b6b3c56d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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