Реакция #3762

Уравнение реакции

1-(2-hydroxy-3-t-butoxycarbonylamino-1-propyl)-4-[[(6R)trans-2-carboxy-8-oxo-7-[(2,5- dichlorophenylthio)acetamido]-5- thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium chloride

Anisole

trifluoroacetic acid

→

title compound

Выход 127.2%

1-(2-Hydroxy-3-amino-1-propyl)-4-[[(6R)-trans-2-carboxy-8-oxo-7-[(2,5-dichlorophenylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium chloride

Выход 127.2%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated in vacuo
2. 2
   workup.STIRRINGThe residue was stirred with ether until a yellow powder
3. 3
   Другоеresulted
4. 4
   ФильтрацияThis solid was collected by filtration
5. 5
   Промывкаwashing with ether
6. 6
   workup.STIRRINGThe crude product was stirred with ether (20 mL) for 45 min
7. 7
   Фильтрацияthe solid was collected by filtration
8. 8
   ФильтрацияThe final filtration

Методика

A slurry of 1-(2-hydroxy-3-t-butoxycarbonylamino-1-propyl)-4-[[(6R)trans-2-carboxy-8-oxo-7-[(2,5- dichlorophenylthio)acetamido]-5- thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium chloride (1.19 g, 1.58 mmol) in methylene chloride (22 mL) was cooled to 0° C. Anisole (3.4 mL) was added followed by trifluoroacetic acid (11 mL). The mixture was stirred for 30 min at 0° C. and 30 min at rt. The reaction mixture was concentrated in vacuo. The residue was stirred with ether until a yellow powder resulted. This solid was collected by filtration washing with ether. The crude product was stirred with ether (20 mL) for 45 min, and then the solid was collected by filtration. This was followed by similar treatments with acetone (1×10 mL) and then ether (1×20 mL). The final filtration gave 655 mg (54%) of the title compound as a yellow solid. 1H NMR (300 MHz, DMSO) δ2.80 (t, J=10, 1H), 3.06 (d, J=11, 1H), 3.31-3.44 (m, 1H), 3.60 (d, J=18, 1H), 3.90 (s, 2H), 4.10 (br s, 1H), 4.34-4.42 (m, 3H), 4.66 (d, J=12, 1H), 5.02 (d, J=5, 1H), 5.56 (t, J=6, 1H), 6.5-7.0 (br s, 1H), 7.21 (dd, J=2, 8, 1H), 7.41-7.46 (m, 2H), 8.12 (m, 2H), 8.30 (br s, 3H), 8.68 (m, 2H), 9.28 (m, 1H); MS (FIA) m/e 615 (MH+); Anal. calcd for C24H24 N4O5S3Cl2.HCl. HO2CCF3 : C, 40.71; H, 3.55; N, 7.30. Found: C, 40.70; H, 3.52; 7.38.

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