2-Methyl-2-butene → HCID 89650339, compound

HRID 1479008Notes

Reaction equation

HRID 1479008 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].CC(=CC)C.[C:16]([O:20][C:21]([N:23]1[CH2:26][CH:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH:34]=[O:35])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>O.O1CCOCC1>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([OH:6])=[O:35])[CH2:26]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 896503653-(2-Formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 89650339HCID 89650339, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (1.85 g; 20.43 mmol; 5.5 eq.) and sodium dihydrogenphosphate (1.6 g; 13.37 mmol; 3.6 eq.) in water (10 mL) was added dropwise to a mixture of 2-methyl-2-butene (3.71 mL) and 3-(2-formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (1.03 g; 3.71 mmol; 1 eq.) in 1,4-dioxane (10 mL). and the reaction mixture was stirred at room temperature for 2 hours. The dioxane was evaporated in vacuo, the mixture diluted with water and the pH made acidic with 0.1M HCl. The precipitate was filtered off, washed with water and dried to afford the title compound (1.02 g, 94%) as a white solid. UPLC/MS: (MS−) 292.4 ([M−H]−).

Workup

  1. customThe dioxane was evaporated in vacuo
  2. additionthe mixture diluted with water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4769957400d4470e89c9d17333a7e736
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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