2-Methyl-2-butene → HCID 9905992, compound

HRID 1357496Notes

Reaction equation

HRID 1357496 reaction equation
Cl([O-])=[O:2].[Na+].[C:5]([NH:8][C@@H:9]1[C@@H:14]([CH2:15][CH:16]=[O:17])[CH2:13][C:12]([C:18]([O:20][CH3:21])=[O:19])=[CH:11][C@H:10]1[O:22][CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])(=[O:7])[CH3:6].CC(=CC)C>OP([O-])(O)=O.[K+].C(O)(C)(C)C>[C:5]([NH:8][C@@H:9]1[C@@H:14]([CH2:15][C:16]([OH:2])=[O:17])[CH2:13][C:12]([C:18]([O:20][CH3:21])=[O:19])=[CH:11][C@H:10]1[O:22][CH:23]([CH2:24][CH3:25])[CH2:26][CH3:27])(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 11723842HCID 11723842, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 9905992HCID 9905992, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 516951Monobasic potassium phosphateSolvent

Procedure

Sodium chlorite (commercial 80%, 16 mg, 0.142 mmol) in 2 mL of KH2PO4 buffer (pH 3-4) was added dropwise to a room temperature solution of Example 7A (36 mg, 0.110 mmol) and 2-methyl-2-butene (118 μL, 1.10 mmol) in tert-butyl alcohol (15 mL). After stirring for 16 hours, the reaction mixture was concentrated. The concentrate was purified by flash chromatography on silica gel using acetic acid/ethyl acetate (1/5) to afford 32 mg (84%) of the desired product as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe concentrate was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-aa8894bfcafe4c3baf7ae416df946161
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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