Ammonium Acetate → {4-[4-Ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid

HRID 533546노트

반응식

HRID 533546 반응식
[CH3:1][C:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]2[O:20]C(C)(C)C(C)(C)[O:17]2)=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])(=O)C.[NH4+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.Cl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([CH3:1])([S:25]([CH3:28])(=[O:26])=[O:27])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]([OH:20])[OH:17])=[CH:12][CH:11]=1)[CH3:7]

참가 물질

6

반응물 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 66578081Ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

생성물 1

HCID 66577887{4-[4-Ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid

시약·촉매·용매 2

HCID 180Acetone용매HCID 313Hydrochloric Acid용매

실험 절차

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate, which may be prepared as in Preparation Number 3, Step A, (4.75 g, 11.5 mmol) in acetone (90 mL) was added ammonium acetate (0.1 M in water, 232 mL, 23.2 mmol) and sodium periodate (7.43 g, 34.7 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with 1N HCl aq. and extracted with ether 2×. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to give {4-[4-ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl]phenyl}boronic acid as an orange oil 3.44 g. LCMS: (M+1) 329.2

후처리

  1. extractionextracted with ether 2×
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0ef9bc9825fa47d3a02c8f5d53477f92
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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