ChemicalBook CAS DataBase List paromamine

paromamine synthesis

7synthesis methods

Product Name:paromamine
CAS Number:534-47-4
Molecular formula:C12H25N3O7
Molecular Weight:323.34

7205-49-4
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534-47-4
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Yield:534-47-4 94%

Reaction Conditions:

with methanol;acetyl chloride at 0 - 70; for 4.41667 h;

Steps:

1

Preparation ofparomamine (Compound 1):Compound 1Compound 1 was prepared by direct Lewis acid promoted cleavage of paromomycin according to the published procedure of Swayze and co-workers [74] with some modifications.Acetyl chloride (35 ml) was added to a stirred solution of anhydrous methanol (215 ml) over 10 minutes at 0 °C. After stirring for about 15 additional minutes, a commercially available paromomycin sulfate sample (25 grams, 31.0 mmol) was added and the reaction was heated to 70 °C under reflux. Propagation of the reaction was monitored by TLC, using a mixture of CH₂Cl₂/MeOH/H₂O/MeNH₂ at a relative ratio of 10:15:6:15 diluted to 33 % solution in ethanol as eluent, which indicated completion after 4 hours. The reaction mixture was cooled for about 2 hours in a freezer, filtered, and the residue was dissolved in a minimal amount of water. This concentrated aqueous solution was added dropwise to cold ethanol (500 ml, 0 ⁰C) and the resulting emulsion was placed in a freezer for about 2 hours. The mixture was filtered and the residue was dried under vacuum to yield Compound 1 as a white solid (12.5 g, 94 % yield).¹H NMR (500 MHz, D₂O, pH=3.5) data of Compound 1 are summarized in the Table 1 below. Table 1¹³C (NMR 125 MHz, D₂O): δ = 30.6 (C-2), 50.6, 51.6, 55.9, 62.1 (C-6'), 71.0, 71.2, 74.3, 75.2, 76.6, 82.7, 98.8 (C-I');MALDI TOFMS calculated for C₁₂H₂₅N₃O₇ Na ([M+Na]⁺) mle: 347..2; measured mle: 347.2.