Hydrochloric Acid → HCID 50925305, compound

HRID 1798329Notes

Reaction equation

HRID 1798329 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:13]([C:16]3[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:22][C:23]([O:25]CC)=[O:24])[O:3]1.[Li+].[OH-].Cl>CCO>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:13]([C:16]3[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:22][C:23]([OH:25])=[O:24])[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 50923083HCID 50923083, compound

Product 1

HCID 50925305HCID 50925305, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(1-hydroxy-4-methyl-6-(1-methyl-1H-pyrazol-5-ylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (100 mg, 0.25 mmol) in EtOH (4 ml) was added aqueous LiOH (1 ml, 10% aq). The mixture was stirred at 0° C. for 3 h. The reaction was acidified with 1N HCl to pH=2-4, extracted with DCM, washed with brine. The organic layer was dried over Na2SO4 and concentrated. Purify via prep. HPLC to get white solid 72 mg. NMR: 1H NMR (DMSO-d6, 400 MHz): δ=12.15 (br, 1H), 9.30 (s, 1H), 8.00 (s, 1H), 7.19 (d, J=2 Hz, 1H), 6.98 (d, J=2 Hz, 1H), 6.80 (d, J=2 Hz, 1H), 5.47 (d, J=6 Hz, 1H), 3.42 (d, J=6 Hz, 1H), 2.25 (s, 3H), 2.12 (d, 1H), 1.03 (s, 3H) ppm. MS (ESI) m/z=365.0 [M−H]−.

Workup

  1. extractionextracted with DCM
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurify via prep

Sources & evidence

ORD record
ord-f061de13f8a3432b9969133ade711486
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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