تفاعل #1702082

معادلة التفاعل

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

المردود 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

المردود 78.7%

المذيبات

DMF

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with saturated sodium bicarbonate and brine
2. 2
   تجفيفThe organic layer was dried over magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by HPLC (Gemini column
6. 6
   أخرىwater, 5 min
7. 7
   أخرىwater, 18 min
8. 8
   أخرى100% acetonitrile, 6 min
9. 9
   workup.ADDITIONboth solvents containing 0.1% trifluoroacetic acid)

الإجراء التجريبي

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).

المصدر