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Potassium Carbonate → {(R)-1-[4-(2-Ethyl-butoxy)-2-methoxy-phenyl]-2-hydroxy-ethyl}-carbamicacid tert-butyl ester

HRID 454969
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HRID 454969 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[O:18][CH3:19])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([CH:23]([CH2:26][CH3:27])[CH2:24]Br)[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:24][CH:23]([CH2:26][CH3:27])[CH2:21][CH3:22])=[CH:13][C:12]=1[O:18][CH3:19])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 77432Pentane, 3-(bromomethyl)-HCID 67073547[(R)-2-Hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 67073758{(R)-1-[4-(2-Ethyl-butoxy)-2-methoxy-phenyl]-2-hydroxy-ethyl}-carbamicacid tert-butyl ester수율 54%

시약·촉매·용매 2

HCID 3283Diethyl Ether
용매
HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To 34 mg (0.122 mmol) of the [(R)-2-hydroxy-1-(4-hydroxy-2-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester and 2-ethylbutylbromide (20 ul, 0.182 mmol) dissolved in 1 ml DMF was added K2CO3 (34 mg, 0.244 mmol) and heated to 60° C. overnight. It was cooled to rt, diluted with ether, and quenched with water. The organic layer was washed with water and brine, and then dried over MgSO4. After removal of the solvent, the residue was purified by flash column (35% EtOAc in hexane) to give the titled compound (24 mg, 54%).

후처리

  1. temperatureIt was cooled to rt
  2. customquenched with water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe residue was purified by flash column (35% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-f596f97c5b684853b73f5db5a4ac8f66
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497271B2

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