Ethanol → Treprostinil diolamine

HRID 922102Notes

Reaction equation

HRID 922102 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:28])[CH2:7][CH2:8][C@H:9]1[C@H:21]([OH:22])[CH2:20][C@H:19]2[C@@H:10]1[CH2:11][C:12]1[C:17]([CH2:18]2)=[C:16]([O:23][CH2:24][C:25]([OH:27])=[O:26])[CH:15]=[CH:14][CH:13]=1.C(O)C.O.[NH:33]([CH2:37][CH2:38][OH:39])[CH2:34][CH2:35][OH:36]>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:28])[CH2:7][CH2:8][C@@H:9]1[C@H:10]2[CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([O:23][CH2:24][C:25]([OH:27])=[O:26])[C:17]=3[CH2:18][C@H:19]2[CH2:20][C@H:21]1[OH:22].[CH2:34]([NH:33][CH2:37][CH2:38][OH:39])[CH2:35][OH:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8113DiethanolamineHCID 6918140Treprostinil

Product 1

HCID 11179459Treprostinil diolamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Treprostinil acid is dissolved in a 1:1 molar ratio mixture of ethanol:water and diethanolamine is added and dissolved. The solution is heated and acetone is added as an antisolvent during cooling.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution is heated
  3. temperatureduring cooling

Sources & evidence

ORD record
ord-36717e2809964bb586bb11aa2d318aef
Source dataset
uspto-grants-2016_03
Patent number
US09278901B2

Reaction notes

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