HCID 67254070, compound → HCID 58292855, compound

HRID 1798148Notes

Reaction equation

HRID 1798148 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[O:12][C:13]1[CH:14]=[C:15]([CH3:27])[C:16]2[CH:20]([CH2:21][C:22]([OH:24])=[O:23])[O:19][B:18]([OH:25])[C:17]=2[CH:26]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:25][B:18]1[C:17]2[CH:26]=[C:13]([O:12][C:11]3[CH:28]=[CH:29][CH:30]=[C:9]([OH:8])[CH:10]=3)[CH:14]=[C:15]([CH3:27])[C:16]=2[CH:20]([CH2:21][C:22]([OH:24])=[O:23])[O:19]1

Participants

4

Reactant 1

HCID 67254070HCID 67254070, compound

Product 1

HCID 58292855HCID 58292855, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.55 g, 1.36 mmol) and 10% Pd/C (0.4 g) in EtOH (100 mL) was hydrogenated at 40 psi for 30 minutes. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (MeOH:DCM 10:90) to give [1-hydroxy-6-(3-hydroxy-phenoxy)-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.25 g, 58%). mp 138.2-140.1° C. 1H NMR (400 MHz, DMSO): δ 12.34 (s, 1H), 9.59 (s, 1H), 9.19 (s, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.09 (d, J=2.0 Hz, 1H), 6.98 (d, J=1.6 Hz, 1H), 6.53 (dd, J=8.4, 2.0 Hz, 1H), 6.42 (dd, J=8.0, 2.0 Hz, 1H), 6.35 (t, J=2.4 Hz, 1H), 5.48 (dd, J=9.2, 2.4 Hz, 1H), 3.09 (dd, J=15.2, 2.4 Hz, 1H), 2.28 (s, 3H), 2.14-2.07 (m, 1H). MS (ESI) m/z: 315 (M+1)+. HPLC purity: 98.56% (Maxplot), 98.87% (220 nm).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography (MeOH:DCM 10:90)

Sources & evidence

ORD record
ord-cea07a488e3b45c58606f49bf9ce79d7
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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