(R)-Methyl 2-amino-3-phenylpropanoate → 3-Azido-3-deoxythymidine 5-methoxy-D-phenylalaninylphosphoramidate

HRID 1016275

Reaktionsgleichung

Reaktionsgleichung von HRID 1016275
[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[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH2:41].C(Cl)(Cl)Cl.[CH3:54][OH:55].[OH2:56]>>[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.[CH3:54][O:55][C:47]1[CH:46]=[CH:45][CH:44]=[C:43]([CH:48]=1)[CH2:42][C@H:40]([C:39]([O:38][P:1]([NH2:25])(=[O:4])[O-:2])=[O:56])[NH2:41]

Komponenten

4

Edukt 3

HCID 853474(R)-Methyl 2-amino-3-phenylpropanoateHCID 21866399Chloroform methanol waterHCID 22892882Triethylammonium 3'-azido-3'-deoxythymidine-5'-phosphite

Produkt 1

HCID 1317236223-Azido-3-deoxythymidine 5-methoxy-D-phenylalaninylphosphoramidateAusbeute 68 %

Versuchsvorschrift

Compound 40 (340 mg, 0.785 mmol) and D-phenylalanine methyl ester (HCl salt, 339 mg, 1.57 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 (282 mg, 68%) as a white solid. 1H NMR (D2O, 300 MHz) 7.415 (s, 1H), 7.1580-6.998 (m, 5H), 5.995 (t, J=6.8 Hz, 1H), 4.118 (m, 1H), 3.808 (m, 1H), 3.738 (m, 1H), 3.661 (m, 1H), 3.467 (m, 1H), 3.403 (s, 3H), 2.754 (m, 2H), 2.212 (m, 2H), 1.679 (s, 3H); 31P NMR (D2O, 121 MHz) 6.204; HRMS (FAB) m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

Quellen und Nachweise

ORD-Eintrag
ord-4e9d8fee7f0b43478ceff445422b529d
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06475985B1

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