ChemicalBook CAS DataBase List CHOLIC ACID METHYL ESTER

CHOLIC ACID METHYL ESTER synthesis

11synthesis methods

Product Name:CHOLIC ACID METHYL ESTER
CAS Number:1448-36-8
Molecular formula:C25H42O5
Molecular Weight:422.6

67-56-1

81-25-4

1448-36-8

To a mixed toluene/methanol (30 ml, V/V=2:1) solution of cholic acid (2.0 g, 4.9 mmol) was added trimethylsilyl diazomethane (3.67 ml, 7.34 mmol), and the reaction was stirred for 2 h at 20 °C. The reaction was monitored by thin layer chromatography (TLC, spreader ratio of methanol/dichloromethane=1:10). The progress of the reaction was monitored by thin layer chromatography (TLC, spreading agent ratio methanol/dichloromethane=1:10) to confirm complete consumption of cholic acid and generation of new spots. Upon completion of the reaction, the reaction mixture was concentrated to afford (R)-methyl 4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthracen-17-yl)pentanoate (2.08 g, 100% yield) as a white foamy solid. Its hydrogen NMR spectrum (400MHz, CDCl3) data were as follows: δ 3.98(m, 1H, C12-H), 3.85(m, 1H, C7-H), 3.45(m, 1H, C3-H), 3.66(s, 3H, OCH3), 0.98(d, 3H, 21-Me), 0.89(s, 3H, 19-Me), 0.69 (s, 3H, 18-Me).

67-56-1 Synthesis

67-56-1
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$9.00/25ml

81-25-4 Synthesis

81-25-4
557 suppliers
$5.00/100mg

1448-36-8
168 suppliers
$5.00/100mg

Yield:1448-36-8 100%

Reaction Conditions:

with diazomethyl-trimethyl-silane in methanol;toluene at 20; for 2 h;

Steps:

1. General procedure for preparation of compound 2

To a solution of compound 1 (2.0 g, 4.9 mmol) in PhCH₃/MeOH (30 ml, V/V=2:1), TMSCHN2(3.67 ml, 7.34 mmol) was added and stirred at 20 °C for 2 h. TLC (MeOH/DCM= 1:10) showed compound 1 was consumed and a new spot was detected. The mixture was concentrated to give compound 2 (2.08 g, 100%) as a white foam solid. HNMR (400MHz, CDCl3) δ (ppm): 3.98 (m, 1H, C12-H), 3.85 (m, 1H, C7-H), 3.45 (m, 1H,C3-H), 3.66 (s, 3H, OCH3), 0.98 (d, 3H, 21-Me), 0.89 (s, 3H, 19-Me), 0.69 (s, 3H, 18-Me).

References:

Thakare, Rhishikesh;Gao, Hongying;Kosa, Rachel E.;Bi, Yi-An;Varma, Manthena V. S.;Cerny, Matthew A.;Sharma, Raman;Kuhn, Max;Huang, Bingshou;Liu, Yiping;Yu, Aijia;Walker, Gregory S.;Niosi, Mark;Tremaine, Larry;Alnouti, Yazen;Rodrigues, A. David [Drug Metabolism and Disposition,2017,vol. 45,# 7,p. 721 - 733] Location in patent:supporting information

81-25-4 Synthesis

81-25-4
557 suppliers
$5.00/100mg