Ethanol → 5795-90-4

HRID 465879Notes

Reaction equation

[C:1]([OH:26])(=[O:25])[CH2:2][CH2:3][C@H:4]([C@@H:6]1[C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][CH2:22]2)[C@:18]2([CH3:19])[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[CH3:5].[CH2:27](O)[CH3:28]>>[CH2:27]([O:25][C:1](=[O:26])[CH2:2][CH2:3][C@H:4]([C@@H:6]1[C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][CH2:22]2)[C@:18]2([CH3:19])[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[CH3:5])[CH3:28]

Participants

Reactant 2

HCID 702Ethanol

HCID 928035beta-Cholan-24-oic acid

Product 1

HCID 2470145795-90-4

Procedure

25 m mol of 5β-cholanic acid was heated in ethanol in the presence of sulfic acid, forming 23 m mol of 5β-cholanic acid ethyl ester. This product was reduced by using lithium aluminum hydride, into 20 m mol of 5β-cholane alcohol. This alcohol, 19 m mol, was subjected to tosylation and then treated with thiourea. The resultant product was treated with bromine water, whereby 10 m mol of 5β-cholanesulfonylbromide was obtained. This compound, 8 m mol, was made to react with 8.5 m mol of nitroaniline. The product of this reaction was subjected to hydrogenation, thus 6.1 m mol of preparing p-amino-5β-cholanesulfonylanilide. This anilide was reacted with cyanogen bromide, and the resultant product was treated with dichloro-dicyanobenzoquinone, thereby obtaining 1.2 m mol of N-5β-cholanesulfonyl-N'-cyano-p-quinonediimine, which is represented by the following formula: ##STR52##

Sources & evidence

ORD record: ord-a1cb422abcd64f75adb0d027247751dd
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153680

Reaction notes

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