HCID 58292560, compound → HCID 58292614, compound

HRID 1798326Notes

Reaction equation

HRID 1798326 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:22][N:21]=[C:20](Cl)[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:22][N:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 58292560HCID 58292560, compound

Product 1

HCID 58292614HCID 58292614, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [6-(3-chloro-[1,2,4]thiadiazol-5-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (400 mg, 1.08 mmol) in MeOH (10 mL) was added Pd/C (300 mg, 75%). The resulting solution was degassed, and reacted under H2 (60 psi) for 2 days. The mixture was filtrated. The filtration was removed in vacuo and purified by column chromatography (silica, DCM/MeOH 4:1) affording the title compound (120 mg, 35%) as a white solid. MS found: (M+H)+: 335.

Workup

  1. customThe resulting solution was degassed
  2. customreacted under H2 (60 psi) for 2 days
  3. filtrationThe mixture was filtrated
  4. filtrationThe filtration
  5. customwas removed in vacuo
  6. custompurified by column chromatography (silica, DCM/MeOH 4:1)

Sources & evidence

ORD record
ord-1ed950d3ef954cc3b5d89ec2b8d8c52e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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