ChemicalBook CAS DataBase List Clarithromycin

Clarithromycin synthesis

9synthesis methods

Product Name:Clarithromycin
CAS Number:81103-11-9
Molecular formula:C38H69NO13
Molecular Weight:747.95

Clarithromycin, (2R,3S,4S, 5R,6R,8R,10R,11R,12S,13R)-3-(2,6-dideoxy- 3-C-3-O-dimethyl-α-L-ribo-hexopyranosyloxy)-6-methoxy-9-oxo-11,12-dihydroxy- 2,4,6,8,10,12-hexamethyl-5-(3,4,6-trideoxy-3-dimethylamino-β-D-xylo-hexopyranosyloxy) cyclopentadecan-13-olide (32.2.2), is a semisynthetic analog of erythromycin A, in which the hydroxyl group at C6 is replaced with a methoxyl group.

Clarithromycin Impurity Q (10 mg) (N-oxide clarithromycin)

118074-07-0
65 suppliers
$71.00/10mg

81103-11-9
731 suppliers
$5.00/100mg

Yield:81103-11-9 96%

Reaction Conditions:

Stage #1: 6-O-methylerythromycin A N-oxidewith tin(ll) chloride in isopropyl alcohol at 30 - 40; for 2 h;
Stage #2: with sodium hydrogencarbonate in water;isopropyl alcohol;

Steps:

3 Example 3; Preparation of clarithromycin by using stannous Chloride Dihydrate as a Reducing Agent

Example 3; Preparation of Clarithromycin by using Stannous Chloride Dihydrate as a Reducing Agent; [00051] 3.82 g(5 mmol) of 6-O-methylerythromycin A N-oxide obtained in Example 1 was suspended in 30 ml of isopropanol. Added thereto was 2.26 g(2.0 mmol) of stannous chloride dihydrate and the mixture was stirred at a temperature ranging from 30 to 40° C. for 2 hours. A saturated sodium bicarbonate solution was added to the resulting mixture and extracted twice with ethylacetate. The combined organic layer was washed with water, dried over anhydrous magnesium sulfate, and then, concentrated under a reduced pressure to obtain 3.60 g of clarithromycin as a white powder in a yield of 96%. [00052] mp: 220223° C.(mp in literature: 222225° C.). [00053] ¹H-NMR (CDCl₃, ppm): δ 5.06(dd, 1H, 13-H), 4.92(d, 1H, 1-H), 4.44(d, 1H, 1'-H), 4.02(dq, 1H, 5-H), 3.78(dd, 1H, 3-H), 3.77(d, 1H, 11-H), 3.67(d, 1H, 5-H), 3.57(ddq, 1H, 5'-H), 3.33(s, 3H, 3-OCH3), 3.20(dd, 1H, 2'-H), 3.072.95(m, 2H, 10-H and 4-H), 3.03(s, 3H, 6-OCH₃), 2.87(dq, 1H, 2-H), 2.58(ddq, 1H, 8-H), 2.40(ddd, 1H, 3'-H), 2.37(d, 1H, 2-Heq), 2.28(s, 6H, 3'-N(CH₃)₂), 2.001.80(m, 3H, 4-H and 7-H₂), 1.41(s, 3H, 18-H), 1.13(s, 3H, 6-CH₃), 0.85(t, 3H, 14-CH₃).

References:

US6809188,2004,B1 Location in patent:Page column 6; 7

50-00-0 Synthesis