Hydrochloric Acid → HCID 67254107, compound

HRID 1798123Notes

Reaction equation

HRID 1798123 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH3:27])[C:14]2[CH:18]([CH2:19][C:20]([O:22]CC)=[O:21])[O:17][B:16]([OH:25])[C:15]=2[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.O.O>[C:1]([O:5][C:6]([CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH3:27])[C:14]2[CH:18]([CH2:19][C:20]([OH:22])=[O:21])[O:17][B:16]([OH:25])[C:15]=2[CH:26]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67253087HCID 67253087, compound

Product 1

HCID 67254107HCID 67254107, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 2-(6-(2-(tert-butoxycarbonyl)ethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (80 mg, 0.2 mmol) in 16 mL of THF/H2O (1/1) was added LiOH (42 mg, 1.0 mmol) in 5 mL of H2O at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified by 1 N HCl to pH=5. The resulting mixture was extracted with EtOAc (3×20 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by prep HPLC to give the title compound as an off-white powder (60 mg, yield: 82.2%). 1H NMR (400 MHz, DMSO) δ12.23 (s, 1H), 9.09 (s, 1H), 7.03 (d, J=2.0 Hz, 1H), 7.01-6.98 (m, 1H), 6.85 (d, J=2.0 Hz, 1H), 5.45-5.42 (m, 1H), 3.96-3.93 (m, 2H), 3.27-3.31 (m, 2H), 3.00-3.04 (m, 1H), 2.25 (s, 3H), 2.08-2.02 (m, 1H), 1.39 (s, 9H); MS (ESI) m/z=366 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×20 ml)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-8c097bc5ca964019803c125655315708
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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