Triacetoxyperiodinane → (1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

HRID 1180775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180775
[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:36])[O:21][CH2:22][C:23]1([CH2:27][O:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([Cl:35])[N:30]=2)[CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C.CCCCCC>ClCCl>[O:13]=[C:3]([NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[C:2]([C@@H:14]([NH:19][C:20](=[O:36])[O:21][CH2:22][C:23]1([CH2:27][O:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([Cl:35])[N:30]=2)[CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1]

Komponenten

6

Edukt 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11489253(1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamateHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 10152540(1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.150 g (0.289 mmol) of (1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate in 2.0 mL of dichloromethane was added 0.031 g (0.375 mmol) of sodium bicarbonate followed by the addition of 0.159 g (0.375 mmol) of Dess-Martin periodinane. The reaction was stirred for 15 min and then poured directly onto a column of silica gel eluting with ethyl acetate:hexane (1:1) to afford 0.1 g (67%) of (1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.31 (m, 6 Hz, 1H), 7.41-7.29 (m, 5H), 7.13 (d, J=7 Hz, 1H), 6.69 (d, J=6 Hz, 1H), 5.29 (d, J=7 Hz, 1H), 5.18-5.08 (m, 2H), 4.41 (s, 2H), 4.20 (s, 2H), 2.07-1.71 (m, 7H), 1.56 (d, J=7 Hz, 3H), 1.26-1.32 (m, 5H), 0.88 (t, J=6 Hz, 3H). LC-MS m/z 517 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-739989ac1d2746f2bebae4cf35bbf524
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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