Potassium Carbonate → (S)-tert-butyl 4-((1,1-diethoxypropan-2-ylamino)methyl)benzo[d]thiazol-2-ylcarbamate
反応式
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].Br[CH2:12][C:13]1[C:18]2[N:19]=[C:20]([N:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:12][C:13]1[C:18]2[N:19]=[C:20]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[S:21][C:17]=2[CH:16]=[CH:15][CH:14]=1)[CH3:6])[CH3:2]参加物
5
反応条件
- 温度
- 65 °C
実験手順
To the solution of (S)-1,1-diethoxypropan-2-amine (Compound XIX-1) 442 mg (3.00 mmol) in acetonitrile 5 ml, 4-bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole (Compound XXI-1) 133 mg (0.30 mmol) and potassium carbonate 62 mg (0.45 mmol) were added and stirred at 65° C. for 2 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate 100 ml and washed with water 100 ml and brine 100 ml. The organic phase was dried with magnesium sulfate 1 g and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain the title compound 173 mg (yield 71%).
後処理
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate 100 ml
- washwashed with water 100 ml and brine 100 ml
- dry with materialThe organic phase was dried with magnesium sulfate 1 g
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified on silica gel column chromatography (chloroform:methanol=100:0 to 95:5)
出典と根拠
- ORDレコード
- ord-b42cde7da68d4b70b264fcd25bba3f1f
- 出典データセット
- uspto-grants-2013_06
- 特許番号
- US08455488B2
反応ノート
読み込み中…