تفاعل #1702086

معادلة التفاعل

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

TMSBr

TMSBr

→

title compound

المردود 62.6%

5-(3,3-Dimethyl-but-1-ynyl)-3[(1-hydroxy-1-oxo-1 λ5phosphinan-4-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

المردود 62.6%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 5 hours
2. 2
   درجة الحرارةbefore cooling to 0° C.
3. 3
   أخرىquenching through the addition of methanol (0.5 ml)
4. 4
   أخرىThe solvent was removed under vacuum
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

5-(3,3-Dimethyl-but-1-ynyl)-3-[(1-methoxy-1-oxo-1λ5-phosphinan-4-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (10 mg, 0.02 mmol) was dissolved in 1 mL of CH2Cl2, and to the solution was added TMSBr (26 μL, 0.2 mmol). The reaction mixture was stirred at room temperature for 40 minutes. Another portion of TMSBr (26 μL, 0.2 mmol) was added and the mixture was stirred at room temperature for 5 hours before cooling to 0° C. and quenching through the addition of methanol (0.5 ml). The solvent was removed under vacuum and 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). This resulted in 6 mg (62%) of the title compound. MS (m/z): 480.2 [M+H]+; HPLC retention time: 3.831 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

المصدر