Reaktion #324599

ord-19cabb8fbeb748948771f233c80370e1

Reaktionsgleichung

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)[C@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
11
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)[C@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Ser-Leu PABC Paclitaxel
C1CCC2=NCCCN2CC1
DBU
→
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)[C@@H](N)CO)C(=O)O
12
Ausbeute 89.0%
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](NC(=O)[C@@H](N)CO)C(=O)O
H-Ser-Leu PABC Paclitaxel
Ausbeute 89.0%

Edukte

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)[C@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
11
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)[C@H](CO)NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O
Fmoc-Ser-Leu PABC Paclitaxel
C1CCC2=NCCCN2CC1
DBU

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe product was precipitated by 1 M HCl in diethyl ether (200 mL)
  2. 2
    Sonstigeit was purified on a silica gel column

Vorschrift

11 (0.1 g, 0.070 mmol) was treated with 1% DBU in THF (3 mL) for 45 seconds at room temperature and the product was precipitated by 1 M HCl in diethyl ether (200 mL) then it was purified on a silica gel column using chloroform/methanol (7:1) to afford 12 (75 mg, 89%) as a white powder. ESI-MS (5 kV, MeOH): m/z (%)=1225.1 (100) [M+Na]+; HPLC (230 nm): >95%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08642555B2uspto-grants-2014_02