Sodium Chloride → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate

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Reaktionsgleichung

[NH2:1][CH2:2][C@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].CCN(CC)CC.[Cl:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34].[Na+].[Cl-]>C(Cl)Cl>[Si:6]([O:5][CH2:4][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:2][NH:1][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][Cl:28])([C:9]([CH3:11])([CH3:12])[CH3:10])([CH3:8])[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

(S)-tert-butyl 1-amino-3-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (1 g, 3.29 mmol) was taken up in 10 mL of CH2Cl2 and cooled to 0° C. To this was added Et3N (0.731 g, 7.24 mmol), followed by 5-chloro-pentanoyl chloride (0.557 g, 3.62 mmol). The reaction mixture was allowed to warm to rt and stirred for 4 h. Upon completion of the reaction, satd NaCl solution was added. The organic layer was extracted with EA, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(5-chloropentanamido)propan-2-ylcarbamate (1.2 g, 86%). 1H NMR (CDCl3, 300 MHz) δ 6.31 (s, 1H), 5.04 (d, 1H), 3.65 (m, 3H), 3.53 (m, 2H), 3.40 (m, 2H), 2.18 (t, 2H), 1.78 (m, 4H), 1.43 (s, 9H), 0.88 (s, 9H), 0.0 (s, 6H).

Aufarbeitung

temperatureto warm to rt
additionwas added
extractionThe organic layer was extracted with EA
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column

Quellen und Nachweise

ORD-Eintrag: ord-cd12be7ff36c4d6aa06377dfb2b1eead
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08487108B2

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