Cesium carbonate → HCID 57494306, compound

HRID 270112Notes

Reaction equation

HRID 270112 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+](C1C=C(S(O[CH2:34][C@@H:35]2[CH2:37][O:36]2)(=O)=O)C=CC=1)([O-])=O>CN1CCCC1=O>[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:12][CH2:34][C@@H:35]2[CH2:37][O:36]2)=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68740825HCID 68740825, compound

Product 1

HCID 57494306HCID 57494306, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(5-chloro-2-hydroxy-4-methoxyphenyl)acetamide (227 mg, 1.05 mmol) and caesium carbonate (376 mg, 1.25 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was added (2S)-oxirane-2-ylmethyl 3-nitrobenzenesulfonate (301 mg, 1.16 mmol) dissolved 2-methyl-2-pyrrolidine (2 mL) drop wise. The resulting brown slurry was stirred over night, at room temperature. The mixture was partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and concentrated to yield crude 280 mg (98%) of the titled compound.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd46fe4c5e2b4f7fb662adf9dd61fa9c
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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