Water → 4-(4-cyclohept-1-en-1-ylphenyl)-N-[(1-methoxypentyl)oxy]-2-methyl-2-(methylsulfonyl)butanamide

HRID 533558Notes

Reaction equation

HRID 533558 reaction equation
[CH3:1][S:2]([C:5]([CH3:33])([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=1)[C:6]([NH:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)=[O:7])(=[O:4])=[O:3].FC(F)(F)S(O[C:40]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH:41]=1)(=O)=O.[C:49](=O)([O-])[O-].[Na+].[Na+].O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[C:40]1([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][C:5]([CH3:33])([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]([NH:8][O:9][CH:10]([O:11][CH3:49])[CH2:15][CH2:14][CH2:13][CH3:12])=[O:7])=[CH:23][CH:22]=2)[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH:41]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 320032Cyclohept-1-en-1-yl trifluoromethanesulfonateHCID 764453942-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-butyramide

Product 1

HCID 866687754-(4-cyclohept-1-en-1-ylphenyl)-N-[(1-methoxypentyl)oxy]-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To flask containing 2-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-butyramide which may be prepared by the method described in Preparation 3 (800 mg, 01.66 mmol) was added cyclohept-1-en-1-yl trifluoromethanesulfonate (812 mg, 3.32 mmol), sodium carbonate (528 mg, 4.99 mmol), water (500 uL) and 1,4-dioxane (4 mL). To this mixture was added pd tetrakis (288 mg, 0.249 mmol) and the mixture was heated to 50° C. with stirring overnight. The mixture was diluted with ethyl acetate and washed with water 2×. The phases were separated, silica gel was added to the organic extracts and the mixture was concentrated to dryness. The crude material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford 4-(4-cyclohept-1-en-1-ylphenyl)-N-[(1-methoxypentyl)oxy]-2-methyl-2-(methylsulfonyl)butanamide as a solid 205 mg. LCMS: (M+1) 448.3.

Workup

  1. custommay be prepared by the method
  2. customdescribed in Preparation 3 (800 mg, 01.66 mmol)
  3. washwashed with water 2×
  4. customThe phases were separated
  5. additionsilica gel was added to the organic extracts
  6. concentrationthe mixture was concentrated to dryness
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-cd583f0abe2f4fb2963a44806176be88
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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