ChemicalBook CAS DataBase List D-Cycloserine

D-Cycloserine synthesis

5synthesis methods

Product Name:D-Cycloserine
CAS Number:68-41-7
Molecular formula:C3H6N2O2
Molecular Weight:102.09

Cycloserine, 4-amino-3-isoxalidinone (34.1.19), can be synthesized both biosynthetically from the actinomycetes Streptomyces garyphalus, Streptomyces orchidaceus, and Streptomyces lavenduale as well as synthetically from the methyl ester of D-serine, the hydroxyl group of which is replaced with a chlorine atom when reacted with phosphorous pentachloride, and subsequent reaction of the resulting product (34.1.19) with hydroxylamine results in heterocyclization to the desired cycloserine (34.1.20).

Acetamide, 2,2,2-trifluoro-N-(3-oxo-4-isoxazolidinyl)-, (R)- (9CI)

144533-21-1
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68-41-7
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Yield:68-41-7 315 mg

Reaction Conditions:

with water;sodium hydroxide in methanol;dichloromethane at 20; for 4 h;

Steps:

(c) Synthesis of compound 6 from compound 3:

Sodium methoxide (12.27 mmol) in MeOH was added to a solution of hydroxylamine hydrochloride (465 mg, 6.69 mmol) in MeOH (10 mL). The mixture was stirred at room temperature for 30 min and cooled to 0 °C. Then the sodium chloride was filtered. A solution of compound 3 (1.2 g, 5.58 mmol) in CH₃CN (20 mL) was added to the filtrate at 0 °C. The mixture was stirred at 0 °C for 4 h and concentrated under reduced pressure. Et₃N (1.16 mL, 8.37 mmol) and CH₂Cl₂ (30 mL) was added to the mixture and stirred at 0 °C for 10 min. Methanesulfonyl chloride (0.73 g, 6.14 mmol) was added next, and the mixture was stirred at 0 °C for 1 h. DBU (1.27 g, 8.37 mmol) was added to the mixture at 0 °C and stirred at room temperature for 2 d. After NaOH (1.12 g, 27 mmol) in water (20 mL) and MeOH (20 mL) were added, the mixture was stirred at room temperature for 4 h. 50 mL of ethanol/isopropyl alcohol was added. The precipitate salts were filtered, and the filtrated was cooled to 0 °C in the ice bath. Glacial acetic acid was added dropwise to the well-stirred mixture to reach pH 6.0 and gave a colorless solid. The crystalline precipitate was filtered and washed twice with 1:1 ethanol/isopropyl alcohol and diethyl ether to give d-4-amino-3-isoxazolidinone (315 mg, 55%). mp 146-148 °C; +110 (c 1.0, H₂O); ¹H NMR (DMSO-d₆, 300 MHz) δ 4.38 (t, 1H), 3.51 (m, 2H); ¹³C NMR (DMSO-d₆, 75 MHz) δ 174.5, 75.1, 53.6; HRMS (ESI) m/z (M+H)⁺ calcd for C₃H₆N₂O₂ = 102.0919, found 102.0743.