Hydroxide → HCID 58355545、化合物

HRID 1184278ノート

反応式

HRID 1184278 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:55]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Na].[OH-:59]>C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].C(N(CC)CC)C>[NH2:55][C@@H:10]1[CH2:11][C@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])=[O:59])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

参加物

8

反応物 4

HCID 961HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 5360545SodiumHCID 58355160HCID 58355160、化合物

生成物 1

HCID 58355545HCID 58355545、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8471Triethylamine溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
100 °C

実験手順

(3R,5S)-1-(tert-Butoxycarbonyl)-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (250 mg) was dissolved in toluene (5 ml), diphenylphosphoryl azide (0.15 ml) and triethylamine (94 μl) were added and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled to room temperature, 8M aqueous sodium, hydroxide solution (0.56 ml) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and the mixture was extracted twice with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) and ethyl acetate-methanol (10:1) was concentrated under reduced pressure to give the object product (155 mg).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (1:1-1:0) and ethyl acetate-methanol (10:1)
  7. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-df26c3e4d383439b96b7e5a417e0a4d8
出典データセット
uspto-grants-2014_03
特許番号
US08664380B2

反応ノート

読み込み中…