Hydrochloric Acid → HCID 58292863, compound

HRID 1798285Notes

Reaction equation

HRID 1798285 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:25]([O:29][C:30]([C:32]1[S:36][C:35](Cl)=[N:34][CH:33]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl>CN(C=O)C>[C:25]([O:29][C:30]([C:32]1[S:36][C:35]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:34][CH:33]=1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 24229786tert-Butyl 2-chloro-1,3-thiazole-5-carboxylateHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292863HCID 58292863, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol), Cs2CO3 (7.82 g, 24 mmol) and t-butyl-2-chloro-1,3-thiazole-5-carboxylate (2.64 g, 12 mmol) in DMF (20 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled down and acidified to pH 3 with 6N HCl, extracted with ethyl acetate and washed with water and brine. The organic layer was dried by Na2SO4 and concentrated. The residue was purified by column chromatography (silica, Hexanes/EA=8:2, then DCM/MeOH=9:1) affording the title compound (3.3 g, 89%) as a light yellow solid. 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.46 (d, 1H), 7.18 (d, 1H), 5.68 (dd, 1H), 4.21 (q, 2H), 3.11 (dd, 1H), 2.44 (m, 1H), 2.39 (s, 3H), 1.56 (s, 9H), 1.24 (t, 3H).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried by Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, Hexanes/EA=8:2

Sources & evidence

ORD record
ord-476dd4c7ee244a4c8a250755c1ab0c56
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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