Diethyl Ether → ergocorninine methanesulfonate

HRID 325287Notes

Reaction equation

HRID 325287 reaction equation
[CH3:1][CH:2]([C@H:4]1[N:13]2[C:14]([C@@:16]([NH:21][C:22]([C@@H:24]3[CH:39]=[C:38]4[C@H:27]([CH2:28][C:29]5[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][C:36]=64)[NH:31][CH:30]=5)[N:26]([CH3:40])[CH2:25]3)=[O:23])([CH:18]([CH3:20])[CH3:19])[O:17][C@@:12]2([OH:41])[C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:5]1=[O:6])=[O:15])[CH3:3].[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].C(OCC)C>C(O)C>[CH3:3][CH:2]([C@H:4]1[N:13]2[C:14]([C@@:16]([NH:21][C:22]([C@@H:24]3[CH:39]=[C:38]4[C@H:27]([CH2:28][C:29]5[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][C:36]=64)[NH:31][CH:30]=5)[N:26]([CH3:40])[CH2:25]3)=[O:23])([CH:18]([CH3:19])[CH3:20])[O:17][C@@:12]2([OH:41])[C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:5]1=[O:6])=[O:15])[CH3:1].[CH3:42][S:43]([OH:46])(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 164671HCID 164671, compound

Product 1

HCID 3057689ergocorninine methanesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ergocorninine (1.50 g; 2.67 mmoles) was dissolved in absolute ethanol (20 ml), containing methanesulfonic acid (0.21 ml; 2.93 mmoles). The clear solution was poured into absolute diethylether (300 ml) while stirring. The precipitated salt was filtered off and dried in vacuo. Ergocorninine methanesulfonate (1.64 g; 98.2% of the theory) with a melting point of 178°-179° C. was obtained.

Workup

  1. filtrationThe precipitated salt was filtered off
  2. customdried in vacuo
  3. custom98.2% of the theory) with a melting point of 178°-179° C. was obtained

Sources & evidence

ORD record
ord-8107cd4756d7446fbf10599a21f738aa
Source dataset
uspto-grants-1984_04
Patent number
US04440772

Reaction notes

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