Hydrochloric Acid → HCID 67253982, compound

HRID 1798128Notes

Reaction equation

HRID 1798128 reaction equation
[F:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([OH:14])=[O:13])[O:8][B:7]([OH:15])[C:6]=2[CH:5]=[C:4]([OH:16])[CH:3]=1.[OH-].[Na+].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O>[CH2:23]([O:22][C:20]([O:16][C:4]1[CH:3]=[C:2]([F:1])[C:10]2[CH:9]([CH2:11][C:12]([OH:14])=[O:13])[O:8][B:7]([OH:15])[C:6]=2[CH:5]=1)=[O:21])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 58292728HCID 58292728, compound

Product 1

HCID 67253982HCID 67253982, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(4-fluoro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)-acetic acid (113 mg, 0.5 mmol) and sodium hydroxide (0.06 g, 1.5 mmol) in water (3 mL) was added ethyl chloroformate (59 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 15 min and then acidified to pH=2 with 1N HCl. The mixture was extracted with ethyl acetate (2×15 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to give the title compound as a white solid (21 mg, Yield: 14%). 1H NMR (400 MHz, DMSO-d) δ9.57 (s, 1H), 7.32-7.37 (m, 2H), 5.59-5.62 (m, 1H), 4.25-4.30 (m, 2H), 2.95-3.00 (m, 1H), 2.36-2.42 (m, 1H), 1.29-1.32 (t, J=6.8 Hz, 3H). MS (ESI) m/z=299 [M+H]+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×15 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-51acb1f0e3044825ae4fcbced97ae091
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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