反応 #1702082

反応方程式

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

収率 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

収率 78.7%

溶媒

DMF

EtOAc

反応条件

後処理

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

実験手順

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).

出典