Hydrochloric Acid → 2-(4-Chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798129Notes

Reaction equation

HRID 1798129 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14]CC)=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18]C(C)C)[CH:3]=1.[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([OH:14])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292846Ethyl 2-(4-chloro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 509230852-(4-Chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-chloro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (200 mg, 0.74 mmol) in 10 mL THF was added LiOH (100 mg, 2.22 mmol) in 5 mL H2O dropwise at 0° C. The mixture was stirred at room temperature for 1.5 h and acidified to pH=5.0 using 1N HCl (8 mL). The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was use directly in next step reaction without further purification.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customdirectly in next step reaction
  5. customwithout further purification

Sources & evidence

ORD record
ord-b3641fc48f274c869139882fbe0ce260
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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