Ingenol → Ingenol Mebutate

HRID 1478952Notes

Reaction equation

HRID 1478952 reaction equation
[CH3:1][C@H:2]1[C@:14]23[CH:17]=[C:18]([CH3:21])[C@H:19]([OH:20])[C@@:13]2([OH:22])[C@H:12]([OH:23])[C:11]([CH2:24][OH:25])=[CH:10][C@H:9]([C:15]3=[O:16])[C@@H:5]2[C:6]([CH3:8])([CH3:7])[C@@H:4]2[CH2:3]1>CS(C)=O>[CH3:12]/[CH:13]=[C:14](\[C:15]([O:20][C@@H:19]1[C@@:13]2([OH:22])[C@H:12]([OH:23])[C:11]([CH2:24][OH:25])=[CH:10][C@H:9]3[C@@H:5]4[C:6]([CH3:8])([CH3:7])[C@@H:4]4[CH2:3][C@@H:2]([CH3:1])[C@:14]2([C:15]3=[O:16])[CH:17]=[C:18]1[CH3:21])=[O:16])/[CH3:2]

Participants

3

Reactant 1

HCID 442042Ingenol

Product 1

HCID 6918670Ingenol Mebutate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(NOTE: Ingenol purity was calculated as 84.18% by quantitative 1H NMR. As ingenol-3-angelate, PEP015, PEP025 and ingenol-3,20-diangelate were provided as solutions in DMSO, purity was not calculated but assumed to be 100%).

Sources & evidence

ORD record
ord-bed63d513b8146a3988c7373bcc283e6
Source dataset
uspto-grants-2016_08
Patent number
US09404131B2

Reaction notes

Loading…