2-Methyl-2-butene → HCID 178441921, compound

HRID 274597Notes

Reaction equation

HRID 274597 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH2:11]([C:15]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)=[C:18]([CH2:38][OH:39])[N:17]([CH:40](C)[CH3:41])[N:16]=1)[CH2:12][CH2:13][CH3:14].CC(=CC)C>O.C1COCC1.C(O)(C)(C)C>[CH2:11]([C:15]1[C:19]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=2)=[C:18]([C:38]([OH:39])=[O:6])[N:17]([CH2:40][CH3:41])[N:16]=1)[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178441917HCID 178441917, compound

Product 1

HCID 178441921HCID 178441921, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium chlorite (80%;0.44 g) and sodium dihydrogen phosphate (0.44 g) in water (5 ml) was added to a mixture of the product of Example 27 (203 mg), 2-methyl-2-butene (2M,0.62 ml) and t-butanol (4 ml) in THF (10 ml) at room temperature. The mixture was stirred vigorously for 20 mins. The mixture was partitioned between ethyl acetate (3×15 ml) and water (15 ml). The combined organic extracts were dried. The solvent was evaporated to give a colourless foam (0.2 g) which was purified by column chromatography on silica gel eluting with System G (50:50:1) to give the title compound as a colourless solid (60 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate (3×15 ml) and water (15 ml)
  2. customThe combined organic extracts were dried
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-188030ea347241f8a1753b3419e4b3dc
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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