反应 #1702082

反应方程式

3-(N-(4-aminocyclohexyl)-4-methylcyclohexanecarboxamido)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid hydrochloride

1-methoxy-1-oxo-1λ5-phosphinan-4-one

Sodium triacetoxyborohydride

→

title compound

收率 78.7%

5-(3,3-Dimethyl-but-1-ynyl)-3-[[4-(1-methoxy-1-oxo-1λ5-phosphinan-4-ylamino)-cyclohexyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

收率 78.7%

溶剂

DMF

EtOAc

反应条件

后处理

1. 1
   洗涤washed with saturated sodium bicarbonate and brine
2. 2
   干燥The organic layer was dried over magnesium sulfate
3. 3
   过滤filtered
4. 4
   浓缩concentrated
5. 5
   其他The residue was purified by HPLC (Gemini column
6. 6
   其他water, 5 min
7. 7
   其他water, 18 min
8. 8
   其他100% acetonitrile, 6 min
9. 9
   workup.ADDITIONboth solvents containing 0.1% trifluoroacetic acid)

实验过程

3-(N-(4-aminocyclohexyl)-4-methylcyclohexanecarboxamido)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid hydrochloride (40 mg, 0.083 mmol) and 1-methoxy-1-oxo-1λ5-phosphinan-4-one (27 mg, 0.166 mmol) were dissolved in 2 mL of DMF. Sodium triacetoxyborohydride (35 mg, 0.166 mmol) was added. The reaction mixture was allowed to stir at room temperature over 18 hours, and then diluted with EtOAc, washed with saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by HPLC (Gemini column; 5% acetonitrile:water, 5 min; 5-100% acetonitrile:water, 18 min; 100% acetonitrile, 6 min; both solvents containing 0.1% trifluoroacetic acid) to give title compound (38.6 mg): MS (m/z): 591.3 [M+H]−; HPLC retention time: 3.28 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

来源