Cholesterol → Dihydroergotamine

HRID 1679036Notes

Reaction equation

HRID 1679036 reaction equation
[CH3:1][C@@:2]1([NH:24][C:25]([C@H:27]2[CH2:42][N:41]([CH3:43])[C@H:40]3[C@@H:29]([C:30]4[C:35]5[C:36]([CH2:39]3)=[CH:37][NH:38][C:34]=5[CH:33]=[CH:32][CH:31]=4)[CH2:28]2)=[O:26])[O:15][C@:14]2([OH:16])[N:5]([C@@H:6]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:7]([N:9]3[C@H:13]2[CH2:12][CH2:11][CH2:10]3)=[O:8])[C:3]1=[O:4].CS(O)(=O)=O.C[C@@H]([C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2CC1)CCCC(C)C.C1OC1.C([O-])(=O)C.[Na+].C(O)(=O)C>O>[CH3:1][C@@:2]1([NH:24][C:25]([C@H:27]2[CH2:42][N:41]([CH3:43])[C@H:40]3[C@@H:29]([C:30]4[C:35]5[C:36]([CH2:39]3)=[CH:37][NH:38][C:34]=5[CH:33]=[CH:32][CH:31]=4)[CH2:28]2)=[O:26])[O:15][C@:14]2([OH:16])[N:5]([C@@H:6]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:7]([N:9]3[C@H:13]2[CH2:12][CH2:11][CH2:10]3)=[O:8])[C:3]1=[O:4]

Participants

6

Reactant 4

HCID 5997CholesterolHCID 6354Ethylene OxideHCID 71171Dihydroergotamine mesylateHCID 23662384Sodium Diacetate

Product 1

HCID 10531Dihydroergotamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 mg of dihydroergotamine mesylate are added together with 1.5 g of cholesterin ethoxylated with approx. 24 mols of ethylene oxide a) to 60 cc of water adjusted to pH 4.1 with a buffer mixture of sodium acetate/acetic acid, and homogenized with a polytron homogenizer. The clear liquid is filled into bottles fitted with droppers.

Workup

  1. additionThe clear liquid is filled into bottles
  2. customfitted with droppers

Sources & evidence

ORD record
ord-130b022a09fb456faddbc73aef3aa100
Source dataset
uspto-grants-1978_03
Patent number
US04078065

Reaction notes

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