Hydrochloric Acid → HCID 58292756, compound

HRID 1798036Notes

Reaction equation

HRID 1798036 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][C@H:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]=2[C@@H:6]([CH2:5][C:4]([OH:18])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292773HCID 58292773, compound

Product 1

HCID 58292756HCID 58292756, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1.00 g, 4.00 mmol) in THF (9 mL) was added a solution of LiOH (0.479 g, 20.0 mmol) in water (8 mL) at 0° C. The resulting mixture was stirred at room temperature for 1.5 hours then acidified to pH=2 with dilute hydrochloric acid and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM/MeOH/AcOH=20:1:trace) to give pure product as a white powder after lyophilization (0.579 g, 64.9%). 1HNMR (400 MHz, DMSO-d) δ12.26 (s, 1H), 9.25 (s, 1H), 9.04 (s, 1H), 6.86 (d, J=1.95 Hz, 1H), 6.64 (d, J=1.95 Hz, 1H), 5.36 (dd, J=9.76, 2.34 Hz, 1H), 2.98 (dd, J=15.22, 2.34 Hz, 1H), 2.17 (s, 3H), 1.98 (dd, 1H). MS (ESI) m/z=221 [M−H]−.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel flash column chromatography (DCM/MeOH/AcOH=20:1:trace)
  3. customto give pure product as a white powder after lyophilization (0.579 g, 64.9%)

Sources & evidence

ORD record
ord-568afcb3c5594a5c8213903f4c8e131c
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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