Hydrochloric Acid → HCID 178429637, compound

HRID 1798330Notes

Reaction equation

HRID 1798330 reaction equation
[N:1]1[N:2]=[C:3]([S:6]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([O:21]CC)=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)(=[O:8])=[O:7])[NH:4][CH:5]=1.[Li+].[OH-].Cl>CCO>[N:1]1[N:2]=[C:3]([S:6]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([OH:21])=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)(=[O:7])=[O:8])[NH:4][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178470808HCID 178470808, compound

Product 1

HCID 178429637HCID 178429637, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(6-(4H-1,2,4-triazol-3-ylsulfonyloxy)-1-hydroxy-4-methyl-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 32 mg. NMR: 1H NMR (DMSO-d6, 400 MHz): δ=12.3 (br, 1H), 9.15 (br, 1H), 8.99 (s, 1H), 7.20 (d, J=2 Hz, 1H), 7.042 (d, J=2 Hz, 1H), 5.48 (dd, J=2.4, 9.2 Hz, 1H), 3.65 (s, 1H), 3.03 (dd, J=2.8, 16.6 Hz, 1H), 2.14 (s, 3H), and 2.1 (q, 1H) ppm. MS (ESI) m/z=352.0 [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-355ec2c7f0ba45b6b854f0fafd6816fe
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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