2-Methyl-2-butene → HCID 89650319, compound

HRID 1479021Notes

Reaction equation

HRID 1479021 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]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[CH:35]=[O:36])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>O.O1CCOCC1>[C:16]([O:20][C:21]([N:23]1[CH2:26][CH:25]([O:27][C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[C:35]([OH:6])=[O:36])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 896501743-(5-Fluoro-2-formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 89650319HCID 89650319, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (1.19 g; 13.13 mmol; 5.5 eq.) and sodium dihydrogenphosphate (1.03 g; 8.59 mmol; 3.6 eq.) in water (7 mL) was added dropwise to a mixture of 2-methyl-2-butene (2.39 mL) and 3-(5-fluoro-2-formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (705 mg; 2.39 mmol; 1 eq.) in 1,4-dioxane (7 mL). The reaction mixture was stirred at room temperature for 16 hours and the 1,4-dioxane concentrated in vacuo. The aqueous solution was diluted with water and the pH made acidic with 0.1M HCl. The precipitate was filtered off and dried to afford the title compound (625 mg, 84%) as a white solid. 1H NMR (CDCl3) δ 8.17 (dd, J=8.8, 6.7 Hz, 1H), 6.85 (ddd, J=8.9, 7.6, 2.3 Hz, 1H), 6.35 (dd, J=9.9, 2.3 Hz, 1H), 5.25-4.87 (m, 1H), 4.41 (ddd, J=10.1, 6.4, 1.2 Hz, 2H), 4.11 (ddd, J=10.0, 4.0, 1.1 Hz, 2H), 1.45 (s, 9H). HPLC (max plot) 96.4%; Rt 3.60 min.

Workup

  1. concentrationthe 1,4-dioxane concentrated in vacuo
  2. additionThe aqueous solution was diluted with water
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-13097e9bf7e34b3fb52c767c5ff49feb
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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