Hydrochloric Acid → HCID 67254070, compound

HRID 1798147Notes

Reaction equation

HRID 1798147 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:25]([O:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:7]2[CH:6]([CH2:5][C:4]([OH:32])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67253499HCID 67253499, compound

Product 1

HCID 67254070HCID 67254070, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.0 g, 2.3 mmol) in THF (20 mL) at 0° C. was added a solution of LiOH (0.278 g, 11.5 mmol) in water (10 mL). The solution was allowed to warm to room temperature and stirred for 3 hours then acidified to pH 2 with 6M HCl. The solution was extracted with ethyl acetate (2×50 mL) and the organic extracts washed with water, brine, dried over sodium sulfate and concentrated in vacuo to give [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid as a clear oil (0.85 g, 91%) which was used without further purification. 1H NMR (400 MHz, DMSO): δ 9.13 (s, 1H), 7.42-7.25 (m, 6H), 7.08 (s, 1H), 6.96 (s, 1H), 6.79 (dd, J=8.4, 2.0 Hz, 1H), 6.64 (s, 1H), 6.51 (d, J=6.8 Hz, 1H), 5.48 (d, J=7.6 Hz, 1H), 5.07 (s, 2H), 3.10 (dd, J=15.6, 2.4 Hz, 1H), 2.26 (s, 3H), 2.13-2.07 (m, 1H).

Workup

  1. extractionThe solution was extracted with ethyl acetate (2×50 mL)
  2. washthe organic extracts washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f11e134e33b44cef9416ea4e8fea5228
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…