Cesium carbonate → HCID 59263279, compound

HRID 643993Notes

Reaction equation

HRID 643993 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:22][C:23]1[N:24]=[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:26][C:27]=1[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:28][C:27]1[O:26][C:25]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[N:24][C:23]=1[CH2:22][S:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 68579346HCID 68579346, compound

Product 1

HCID 59263279HCID 59263279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the title B compound, 2-(4-mercaptobenzene-sulfonylamino)-benzoic acid (200 mg, 0.65 mmol), 4-chloromethyl-5-methyl-2-phenyl-oxazole (134 mg, 0.65 mmol) and cesium carbonate (1.05 g, 3.24 mmol) in DMF is stirred at RT for 3 h. The mixture is then partitioned between EtOAc and 1 N aqueous HCl. The organic phase is dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue is chromatographed on silica gel using 15% EtOAc in hexane (containing 0.5% formic acid) as the eluent to afford 2-[4-(5-methyl-2-phenyl-oxazol-4-ylmethylsulfanyl)-benzenesulfonyl-amino]-benzoic acid as a white foam: m.p. 182-184° C.; ESI-MS 481 [M+1]+.

Workup

  1. customThe mixture is then partitioned between EtOAc and 1 N aqueous HCl
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel using 15% EtOAc in hexane (containing 0.5% formic acid) as the eluent

Sources & evidence

ORD record
ord-addacb6f7b434417ab43be05c766055e
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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