2-Methyl-2-butene → HCID 89253167, compound

HRID 923546Notes

Reaction equation

HRID 923546 reaction equation
[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:34][CH2:35][CH2:36][CH:37]=[O:38])[C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(=CC)C.Cl([O-])=[O:47].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:34][CH2:35][CH2:36][C:37]([OH:47])=[O:38])[C:24](=[O:33])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 89253130HCID 89253130, compound

Product 1

HCID 89253167HCID 89253167, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirring solution of 4-((4-methoxy-N-(4-oxobutyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-8 (264 mg, 0.484 mmol) in tert-butanol (12 mL) was added 2-methylbut-2-ene (4.7 ml, 44.4 mmol). A solution of sodium chlorite (400 mg, 4.42 mmol) and sodium dihydrogen phosphate (400 mg, 3.33 mmol) in H2O (2.5 mL) were added and the reaction stirred for 1 h at room temperature. The reaction was quenched with aq. Na2S2O5 (10 mL) and brine (10 mL). The aqueous phase was extracted with DCM and the combined organic phases were dried over MgSO4 and concentrated. The crude product was purified by chromatography (EA/hexanes) to provide 150 mg (55%) of 4-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-methoxybenzamido)butanoic acid 88. LCMS-ESI (m/z) calculated for C33H39NO7: 561; found 560 [M−H]−, tR=9.53 min (Method 4).

Workup

  1. customThe reaction was quenched with aq. Na2S2O5 (10 mL) and brine (10 mL)
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-23d35bc6149c4c37bb8db359800d744b
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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