558-42-9 ,Some common heterocyclic compound, 558-42-9, molecular formula is C4H9ClO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A solution of (5S)-N2, N2-bis (tert-butoxycarbonyl)-5- (2, 3-difluorophenyl)-D-lysine (0.569 g, 1.24 MMOL), 1-CHLORO-2-METHYL-2-PROPANOL (0.202 g, 1.86 mmol) and DIISOPROPYLETHYLAMINE (0.529 g, 4.10 mmol) in ETOH (5 mL) was heated at 75 oC overnight. The reaction was concentrated to dryness, diluted with DCM (20 mL) and EDC (0.358 g, 1.87 mmol), HOAT (0.252 g, 1.87 mmol) were added followed by DIISOPROPYLETHYLAMINE (0.650 ML, 3.73 MMOL). After stirring overnight, NAHCO3 was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered, concentrated and the residue purified by silica gel chromatography (10percent- 35percent EtOAc/ hexanes) to give the title compound (0.21 g). MS 513.1 (M+1). H NMR (500 MHz, CD30D) 5 7.1 (M, 3H), 5.24 (d, J = 10.7 Hz, 1H), 4.02 (M, 1H), 3.69 (d, J = 13.9 Hz, 1H), 3.60 (d, J = 15. 1 Hz, 1H), 3.39 (m, 1H), 3. 24 (d, J = 14.2 Hz, 1H), 2.4 (m, 1H), 2.1 (m, 3H), 1.5 (s, 18H), 1.20 (s, 3H), 1.16 (s, 3H).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 558-42-9.
Reference:
Patent; MERCK & CO., INC.; WO2004/92166; (2004); A2;,
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