反応式
[CH2:1]([O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13](B4OC(C)(C)C(C)(C)O4)=[CH:14][CH:15]=3)[C@@:10]3([CH2:33][O:32][C:31]([NH2:34])=[N:30]3)[C:9]=2[CH:8]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].Br[C:36]1[NH:37][CH:38]=[CH:39][N:40]=1.CC([O-])=O.[K+].CC(N)CC1C=CC=CC=1.OP(O)(O)=O>C(O)CCC.O.CO>[NH:37]1[CH:38]=[CH:39][N:40]=[C:36]1[C:13]1[CH:14]=[CH:15][C:16]2[O:17][C:18]3[C:9](=[CH:8][C:7]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:20][CH:19]=3)[C@:10]3([CH2:33][O:32][C:31]([NH2:34])=[N:30]3)[C:11]=2[CH:12]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 120 °C
実験手順
A solution of (S)-2′-(neopentyloxy)-7′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (50 mg, 0.108 mmol) in BuOH (861 μL), 2-bromo-1H-imidazole (0.129 mmol), and KOAc (31.7 mg, 0.323 mmol) in Water (215 μL) was purged with Ar in a sealed tube. AmPhos (1.525 mg, 2.153 μmol) was added and the reaction was heated to 120° C. for 30 min in the microwave. The reaction was cooled to rt, diluted with MeOH (3 ml), loaded onto an AccuBOND II SCX cartridge, washed with MeOH (3 ml) and eluted with 2N NH3 in MeOH (6 ml) to give the crude product which was purified by reverse-phase preparative HPLC using a Gemini NX c!8 column (150*30 mm, 5 um), 0.1% TFA in CH3CN/H2O, gradient 0% to 70% over 10 min to provide (S)-2′-(1H-imidazol-2-yl)-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine.
後処理
- temperatureThe reaction was cooled to rt
- washwashed with MeOH (3 ml)
- washeluted with 2N NH3 in MeOH (6 ml)
- customto give the crude product which
- customwas purified by reverse-phase preparative HPLC
- customover 10 min
出典と根拠
- ORDレコード
- ord-813580b86bc541abab42e4b658d2d333
- 出典データセット
- uspto-grants-2014_11
- 特許番号
- US08883782B2
関連ノート
読み込み中…