Benzyl chloroformate → (1-Cyano-2-methanesulfonyl-1-methyl-ethyl)-carbamic acid benzyl ester
Reaktionsgleichung
[NH2:1][C:2]([CH3:10])([CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[C:3]#[N:4].CCN(C(C)C)C(C)C.[C:20](Cl)(=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:21][C:20](=[O:29])[NH:1][C:2]([C:3]#[N:4])([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 45 °C
Versuchsvorschrift
To a solution of 2-Amino-3-methanesulfonyl-2-methyl-propionitrile (Example 80a, 5.01 g, 30.9 mmol) in dry THF (119 mL) was added DIEA (12.1 mL, 67.9 mmol) and benzyl carbonochloridate (CAN 501-53-1, 5.57 mL, 37.1 mmol). Reaction was stirred at 45° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and was extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (8.12, 89%) as a yellow oil. MS (ESI, m/z): 297.5 (M+H+).
Aufarbeitung
- customReaction
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionThe residue was dissolved in ethylacetate
- extractionwas extracted with an 1.0M aqueous solution of sodium bicarbonate
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated down to dryness
- customThe crude was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient
Quellen und Nachweise
- ORD-Eintrag
- ord-ac3eb25091604f1da2dc47aee08679fb
- Quelldatensatz
- uspto-grants-2016_08
- Patentnummer
- US09409866B2
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