Ethyl Acetate → HCID 70873766, compound

HRID 2208946Notes

Reaction equation

HRID 2208946 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[C:15](=O)([O-])[O-].[Cs+].[Cs+].I[CH:22]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]1.C(OCC)(=O)C>C(#N)C.O>[CH3:15][O:8][C:7]([C:6]1[CH:10]=[C:2]([CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=1[CH3:11])[O:1][CH:22]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]1)=[O:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 178429609HCID 178429609, compound

Product 1

HCID 70873766HCID 70873766, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To stirred solution of 5-hydroxy-2-methyl-3-nitrobenzoate (1.5 g, 7.1 mmol) in ACN (15 mL) were added cesium carbonate (4.64 g, 14.2 mmol) and tert-butyl 3-iodoazetidine-1-carboxylate (3.0 g, 11 mmol). The resulting mixture was heated at 80° C. overnight. On completion, the reaction mixture was diluted with water and extraction was carried out using ethyl acetate. The combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (1.2 g, 46%).

Workup

  1. washThe combined organic layers were washed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-13f3439ee73748e68db936c07ec05875
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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