Cesium carbonate → HCID 131724881, compound

HRID 2181571Notes

Reaction equation

HRID 2181571 reaction equation
[Cl:1]C1C=CC(S[C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3([C:24]([NH:26][OH:27])=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=CC=1.[N:28]1([C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)[CH:32]=[N:31][CH:30]=[N:29]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[ClH:1].[OH:27][NH:26][C:24]([C:18]1([S:15]([C:12]2[CH:13]=[CH:14][C:9]([O:39][C:36]3[CH:35]=[CH:34][C:33]([N:28]4[CH:32]=[N:31][CH:30]=[N:29]4)=[CH:38][CH:37]=3)=[CH:10][CH:11]=2)(=[O:16])=[O:17])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)=[O:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1100644-(1,2,4-Triazol-1-yl)phenolHCID 9910421HCID 9910421, compound

Product 1

HCID 131724881HCID 131724881, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Part A: To a solution of the protected hydroxamate of Example 25, part B (2.9 g, 7.5 mmol) in DMF (10 mL) was added 4-(1,2,4-triazol-1-yl)phenol (2.47 g, 15 mmol) in DMF (5 mL) followed by Cs2CO3 (7.33 g, 22.5 mmol), and the solution was heated at 95 degrees Celsius for 5 hours. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated NaCl and dried over Na2SO4. Chromatography (on silica, ethyl acetate/hexane/methanol) provided the phenol as a white solid (3.16 g, 80%).

Workup

  1. temperaturethe solution was heated at 95 degrees Celsius for 5 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and H2O
  4. washThe organic layer was washed with saturated NaCl
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-56d1a16cf2db4b28a32b32656f3e93cc
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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