L-Tryptophan, methyl ester → 3-Azido-3-deoxythymidine 5-methoxy-L-trytophanyl-phosphoramidate

HRID 1016274

Reaktionsgleichung

Reaktionsgleichung von HRID 1016274
[P:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[N:20]=[N+:21]=[N-:22])([O-])[O-:2].C([NH+:25](CC)CC)C.C([NH+](CC)CC)C.C[O:38][C:39](=O)[C@H:40]([CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)[NH2:41].C(Cl)(Cl)Cl.[CH3:57][OH:58].[OH2:59]>>[CH3:18][C:17]1[C:15](=[O:16])[NH:14][C:12](=[O:13])[N:11]([C@@H:9]2[O:10][C@H:6]([CH2:5][OH:4])[C@@H:7]([N:20]=[N+:21]=[N-:22])[CH2:8]2)[CH:19]=1.[CH3:57][O:58][C:49]1[CH:50]=[C:51]2[C:46]([NH:45][CH:44]=[C:43]2[CH2:42][C@@H:40]([C:39]([O:38][P:1]([NH2:25])(=[O:4])[O-:2])=[O:59])[NH2:41])=[CH:47][CH:48]=1

Komponenten

4

Edukt 3

HCID 77980L-Tryptophan, methyl esterHCID 21866399Chloroform methanol waterHCID 22892882Triethylammonium 3'-azido-3'-deoxythymidine-5'-phosphite

Produkt 1

HCID 1317236203-Azido-3-deoxythymidine 5-methoxy-L-trytophanyl-phosphoramidateAusbeute 70 %

Versuchsvorschrift

Compound 40 (218 mg, 0.503 mmol) and tryptophan methyl ester (HCl salt, 258 mg, 1.01 mmol) were subjected to a procedure similar to that described in Example 6. Flash chromatography (SiO2, 5:2:0.25 CHCl3/MeOH/H2O containing 0.5% conc. NH4OH) gave the title compound (198 mg, 70%) as a white solid. 1H NMR (D2O, 300 MHz) 7.222 (d, J=7.9 Hz, 1H), 7.103 (d, J=8.1 Hz, 1H), 7.072 (s, 1H), 6.880 (s, 1H), 6.857 (t, J=7.7 Hz, 1H), 6.729 (t, J=7.5 Hz, 1H), 5.690 (t, J=6.6 Hz, 1H), 3.883 (m, 1H), 3.763 (m, 1H), 3.635 (m, 1H), 3.527 (m, 2H), 3.448 (s, 3H), 2.899 (m, 1H), 2.765 (m, 1H), 1.857 (m, 1H), 1.682 (m, 1H), 1.493 (s, 3H); 31P NMR (D2O, 121 MHz) 6.412; HRMS (FAB) m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

Quellen und Nachweise

ORD-Eintrag
ord-8cd77d15167643078f48eb287c942fac
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06475985B1

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