Hydrochloric Acid → 13844-22-9

HRID 1518924Notes

Reaction equation

C/C=C(/C([O:7][C@@H:8]1[C:69]([CH3:71])([CH3:70])[CH2:68][CH:67]2[C@@:10]([CH2:74][OH:75])([C@H:11]([OH:73])[CH2:12][C@@:13]3([CH3:72])[C@:18]4([CH3:66])[CH2:19][CH2:20][CH:21]5[C@:26]([CH2:28][OH:29])([CH3:27])[CH:25]([O:30][C@@H]6O[C@H](C(O)=O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[CH2:24][CH2:23][C@:22]5([CH3:65])[CH:17]4[CH2:16][CH:15]=[C:14]32)[C@H:9]1[O:76]C(C)=O)=O)\C.C/C=C(\C(O[C@@H:87]1[C:148](C)([CH3:149])[CH2:147][CH:146]2[C@@:89](CO)([C@H:90]([OH:152])[CH2:91][C@@:92]3([CH3:151])[C@:97]4([CH3:145])[CH2:98][CH2:99][CH:100]5[C@:105]([CH2:107][OH:108])([CH3:106])[CH:104]([O:109][C@@H]6O[C@H](C(O)=O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[CH2:103][CH2:102][C@:101]5([CH3:144])[CH:96]4[CH2:95][CH:94]=[C:93]32)[C@H:88]1[O:155]C(C)=O)=O)/C.Cl.[CH2:160]([OH:162])[CH3:161]>>[CH3:70][C:69]1([CH3:71])[CH:8]([OH:7])[CH:9]([OH:76])[C:10]2([CH2:74][OH:75])[CH:67]([C:14]3[C:13]([CH3:72])([CH2:12][CH:11]2[OH:73])[C:18]2([CH3:66])[CH:17]([C:22]4([CH3:65])[CH:21]([CH2:20][CH2:19]2)[C:26]([CH2:28][OH:29])([CH3:27])[CH:25]([OH:30])[CH2:24][CH2:23]4)[CH2:16][CH:15]=3)[CH2:68]1.[CH3:144][C@@:101]12[C@H:96]3[CH2:95][CH:94]=[C:93]4[C@@H:146]5[CH2:147][C:148]([CH3:149])([CH3:87])[C@@H:161]6[O:152][C@@H:90]([C@@:89]5([CH2:88][OH:155])[C@H:160]6[OH:162])[CH2:91][C@@:92]4([CH3:151])[C@:97]3([CH3:145])[CH2:98][CH2:99][C@H:100]1[C@:105]([CH2:107][OH:108])([CH3:106])[C@@H:104]([OH:109])[CH2:103][CH2:102]2

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 6433489Escin

Product 2

HCID 61200913844-22-9

HCID 15558431HCID 15558431, compound

Procedure

In Justus Liebigs Annalen der Chemie 1963, 669, 183-188 Kuhn R. and Loew I. described the hydrolysis of escin in the solution of 4 N hydrochloric acid in ethanol, the separation of the intermediate, and its subsequent hydrolysis under basic conditions with potassium hydroxide in methanol. The hydrolysis products were separated by chromatography on silica gel, yielding protoescigenin and escigenin.

Workup

customthe separation of the intermediate, and its subsequent hydrolysis under basic conditions with potassium hydroxide in methanol
customThe hydrolysis products were separated by chromatography on silica gel

Sources & evidence

ORD record: ord-e9b74c31e05d49879ad7b2276ebe75fa
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073813B2

Reaction notes

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