3-ALPHA-HYDROXY-6-OXO-5-ALPHA-CHOLAN-24-OIC ACID METHYL ESTER 3-ACETATE synthesis

8synthesis methods

Product Name:3-ALPHA-HYDROXY-6-OXO-5-ALPHA-CHOLAN-24-OIC ACID METHYL ESTER 3-ACETATE
CAS Number:2616-79-7
Molecular formula:C27H42O5
Molecular Weight:446.62

Cholan-24-oic acid, 3-hydroxy-6-oxo-, methyl ester, (3α,5α)-

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3-ALPHA-HYDROXY-6-OXO-5-ALPHA-CHOLAN-24-OIC ACID METHYL ESTER 3-ACETATE

2616-79-7
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$313.00/500mg

Yield:2616-79-7 95%

Reaction Conditions:

with pyridine;dmap in dichloromethane at 20; for 0.5 h;

Steps:

Methyl 3α-acetoxy-6-oxo-5α-cholan-24-oate (12)

To a solution of compound 8 (2.00g, 4.94 mmol) in 20 mLof DCM, 5 mg of DMAP, 1 mL of pyridine and 0.5 mL (5.3 mmol) of Ac2O were added. The reactionmixture was kept under constant stirring and room temperature for 30 min. The end of reactionwas verified by TLC, the mixture was then concentrated to a volume approximately 5 mL underreduced pressure. Then AcOEt (30 mL) were added. The organic layer was washed with water(2 x15 mL), dried over Na2SO4, and filtered. The solvent was evaporated under reduced pressure andthe crude was re-dissolved in CH2Cl2 (5 mL) and chromatographed on silica gel with EtOAc/hexanemixtures of increasing polarity (0.2:9.8 →4.7:5.3). Compound 12 (1.9 g, 95% yield) was a colorlesssolid (m.p. = 174-176 °C, MeOH/Et2O) IR (cm1): 2943 (CH3); 2869 (CH2); 1737 (C=O); 1708 (C=O);1435 (CH2); 1376 (CH3); 1262 (C-O); 1221 (C-O); 1172 (C-O). 1H-NMR: 5.12 (m, 1H, H-3); 3.66 (s, 3H,CH3O); 2.56 (dd, J = 3.3 and 12.0 Hz, 1H, H-5); 2.38 (ddd, J = 5.4, 10.3 and 15.4 Hz, 1H, H-23); 2.04 (s,3H, CH3CO); 0.94 (d, J = 6.4 Hz, 3H, H-21); 0.74 (s, 3H, H-19); 0.67 (s, 3H, H-18). 13C-NMR: See Table 1.1H-NMR and 13C-NMR are shown in Supplementary Materials.

References:

Herrera, Heidy;Carvajal, Rodrigo;Olea, Andrés F.;Espinoza, Luis [Molecules,2016,vol. 21,# 9,art. no. 1139]