Reacción #324598

ord-8c1d3a206c64464f833a20ec8b9f0da5

Ecuación de reacción

CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
8
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Leu PABC Paclitaxel
C1CCC2=NCCCN2CC1
1,8-Diazabicyclo[5.4.0]undec-7-en
→
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](N)C(=O)O
9
Rendimiento 84.0%
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](N)C(=O)O
H-Leu PABC Paclitaxel
Rendimiento 84.0%

Reactantes

CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
8
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O.CC(C)(NCC(O)COc1cccc2[nH]c3ccccc3c12)c1ccc(N=[N+]=[N-])cc1.CC(C)C[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Leu PABC Paclitaxel
C1CCC2=NCCCN2CC1
1,8-Diazabicyclo[5.4.0]undec-7-en

Reactivos

Ninguno

Disolventes

C1CCOC1
Tetrahydrofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe product was precipitated by 1 M HCl in diethyl ether (500 mL)
  2. 2
    OtroThen it was purified on a silica gel column

Procedimiento

8 (0.50 g, 0.37 mmol) was treated with 1% of 1,8-Diazabicyclo[5.4.0]undec-7-en (DBU) in Tetrahydrofuran (THF) (10 mL) for 45 seconds at room temperature and the product was precipitated by 1 M HCl in diethyl ether (500 mL). Then it was purified on a silica gel column using chloroform/methanol (7:1) to afford 9 (350 mg, 84%) as a white powder. ESI-MS (5 kV, MeOH): m/z (%)=1116.1 (100) [M+H]+; HPLC (230 nm): >95%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08642555B2uspto-grants-2014_02