Potassium Phosphate, Tribasic → tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

HRID 923456

반응식

HRID 923456 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:25]1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)[CH2:30]CCC[CH2:26]1.C(/B(O)O)=C/C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH:26](/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:25]/[CH3:30]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 118318066tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate수율 648.7%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixed liquid of 1.50 g of tert-butyl(2-bromobenzyl)carbamate, 3.90 g of tripotassium phosphate, 348 mg of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, 195 mg of tris(dibenzylideneacetone)dipalladium(0), 905 mg of (1Z)-prop-1-en-1-yl boronic acid, 30 ml of 1,4-dioxane, and 7.5 ml of water was stirred at 90° C. for 15 hours. The reaction mixture was left to be cooled to room temperature and then filtrated over Celite. The filtrate was concentrated under reduced pressure, and then to the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain 1.36 g of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate.

후처리

  1. waitThe reaction mixture was left
  2. filtrationfiltrated over Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionto the reaction mixture was added water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ec9a003cbe024598972d82f1b2c6d7b6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278968B2

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