Diethyl Ether → Ergotaminine methanesulfonate

HRID 325290Notes

Reaction equation

HRID 325290 reaction equation
[CH3:1][C@@:2]1([NH:24][C:25]([C@H:27]2[CH:42]=[C:41]3[C@@H:30]([CH2:31][C:32]4[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]=53)[NH:34][CH:33]=4)[N:29]([CH3:43])[CH2:28]2)=[O:26])[O:15][C@:14]2([OH:16])[N:5]([C@@H:6]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]([N:9]3[C@H:13]2[CH2:12][CH2:11][CH2:10]3)=[O:8])[C:3]1=[O:4].[CH3:44][S:45]([OH:48])(=[O:47])=[O:46].C(OCC)C>C(O)C>[CH3:1][C@@:2]1([NH:24][C:25]([C@@H:27]2[CH:42]=[C:41]3[C@H:30]([CH2:31][C:32]4[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]=53)[NH:34][CH:33]=4)[N:29]([CH3:43])[CH2:28]2)=[O:26])[O:15][C@:14]2([OH:16])[N:5]([C@@H:6]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]([N:9]3[C@H:13]2[CH2:12][CH2:11][CH2:10]3)=[O:8])[C:3]1=[O:4].[CH3:44][S:45]([OH:48])(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 115248Ergotaminine

Product 1

HCID 3057691Ergotaminine methanesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ergotaminine (1.25 g; 2.15 mmoles) was dissolved in absolute ethanol (53 ml), containing methanesulfonic acid (0.16 ml; 2.46 mmoles). The clear solution was poured into absolute diethylether (430 ml). The precipitated salt was filtered off and dried in vacuo. Ergotaminine methanesulfonate (1.3 g; 99.2% of the theory) with a melting point of 184°-187° C. was obtained.

Workup

  1. filtrationThe precipitated salt was filtered off
  2. customdried in vacuo
  3. custom99.2% of the theory) with a melting point of 184°-187° C. was obtained

Sources & evidence

ORD record
ord-f6e97f6a3f5041629b52f5ec32dc61da
Source dataset
uspto-grants-1984_04
Patent number
US04440772

Reaction notes

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