Hydrochloric Acid → [2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid tert.-butyl ester

HRID 1926946ノート

反応式

HRID 1926946 の反応式
[OH-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([O:20][CH2:21][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:23][OH:24])=[N:17][CH:16]=[N:15][C:14]=3[O:13][C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:7][CH:6]=1)[CH3:4].[C:35]([O:39][C:40](=[O:43])[CH2:41]Br)([CH3:38])([CH3:37])[CH3:36].Cl>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:35]([O:39][C:40](=[O:43])[CH2:41][O:24][CH2:23][CH:22]([CH2:21][O:20][C:18]1[C:19]2[C:11]([C:8]3[CH:7]=[CH:6][C:5]([CH2:3][CH3:4])=[CH:10][CH:9]=3)=[C:12]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[O:13][C:14]=2[N:15]=[CH:16][N:17]=1)[C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:38])([CH3:37])[CH3:36]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 580168362-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol

生成物 1

HCID 58016779[2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid tert.-butyl ester

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

Add 0.5 ml of 11.25 N sodium hydroxide solution to a solution of 265 mg (0.62 mmol) 2-({[5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol in 10 ml toluene. After adding 21 mg (0.06 mmol) tetra-n-butylammonium hydrogensulphate and 240 mg (1.23 mmol) 2-bromoacetic acid tert.-butyl ester, stir the reaction mixture for 16 h at 70° C. After cooling to room temperature, neutralize with 1 N hydrochloric acid and extract with ethyl acetate. Wash the organic phase with satd. aqueous sodium chloride solution, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 170 mg (51% of theor.) of the desired product (racemate) is obtained.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextract with ethyl acetate
  3. washWash the organic phase with satd
  4. dry with materialaqueous sodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. customby vacuum evaporation
  8. customPurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

出典と根拠

ORDレコード
ord-281514177254418296658c5e5966b362
出典データセット
uspto-grants-2012_05
特許番号
US08183246B2

反応ノート

読み込み中…