Sodium Azide → 5-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2-({1-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714710ノート

反応式

HRID 714710 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:17])([F:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1B(O)O.[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:39]([CH2:47][C@H:48]([OH:53])[C:49]([F:52])([F:51])[F:50])[C:40](=[O:46])[N:41]([CH2:43][C:44]#[CH:45])[N:42]=2)=[CH:34][CH:33]=1>CO.O.C(OCC)(=O)C.[OH-].[Na+].O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:39]([CH2:47][C@H:48]([OH:53])[C:49]([F:51])([F:52])[F:50])[C:40](=[O:46])[N:41]([CH2:43][C:44]3[N:1]=[N:2][N:3]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[C:6]([F:17])([F:16])[F:5])[CH:45]=3)[N:42]=2)=[CH:34][CH:33]=1

参加物

10

反応物 4

HCID 33557Sodium AzideHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 66586226sodium L-ascorbic acidHCID 866909105-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 866909335-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2-({1-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

試薬・触媒・溶媒 5

HCID 165397Cupric acetate monohydrate触媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

20 mg (0.31 mmol) of sodium azide were initially charged in 1 ml of methanol, and 58 mg (0.31 mmol) of 2-(trifluoromethyl)phenylboronic acid and 6 mg (0.03 mmol) of copper(II) acetate monohydrate were added. The mixture was stirred at RT for 18 h. 0.9 ml of water, 30 mg (0.15 mmol) of L-ascorbic acid sodium salt and 117 mg (0.34 mmol) of the compound from Example 14A were then added to the mixture. The mixture was stirred at RT for a further 18 h. For work-up, the mixture was diluted with 10 ml of water and 10 ml of ethyl acetate, and 5 ml 0.1 N aqueous sodium hydroxide solution were added with stirring. After phase separation, the aqueous phase was extracted three more times with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1, then 1:2). This gave 117 mg (71% of theory) of the target compound.

後処理

  1. stirringThe mixture was stirred at RT for a further 18 h
  2. additionwere added
  3. stirringwith stirring
  4. customAfter phase separation
  5. extractionthe aqueous phase was extracted three more times with in each case 10 ml of ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on silica gel (mobile phase

出典と根拠

ORDレコード
ord-b6eec341133f462bbff55dee25ccef0e
出典データセット
uspto-grants-2015_11
特許番号
US09187466B2

反応ノート

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