Hydrochloric Acid → HCID 58292628, compound

HRID 1798076Notes

Reaction equation

HRID 1798076 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([O:21]CC)=[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.[OH-].[Li+].Cl>CCO.O>[CH2:1]([O:8][C:9]1[C:17]2[CH:16]([CH2:18][C:19]([OH:21])=[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292665HCID 58292665, compound

Product 1

HCID 58292628HCID 58292628, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-(benzyloxy)-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (195 mg, 0.57 mmol) in EtOH (4 mL) was added dropwise an aqueous solution of lithium hydroxide (47.9 mg, 1.14 mmol) in water (4 mL). The reaction mixture was stirred at room temperature overnight and acidified with 1N HCl to pH=3. The resulting mixture was extracted with EtOAc (2×20 mL). Combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (41.2 mg, Yield: 23%). 1H NMR (400 MHz, CDCl3) δ 9.46 (s, 1H), 9.14 (s, 1H), 7.44-7.33 (m, 5H), 6.66 (d, J=1.2 Hz, 1H), 6.54 (s, 1H), 5.36 (m, 1H), 5.12 (s, 2H), 3.15 (m, 1H), 2.07 (m, 1H). MS (ESI) m/z=315 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-92ec3b61640f4da49b5a17675a84c27c
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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