Ethanol → Treprostinil diolamine

HRID 2170018Notes

Reaction equation

HRID 2170018 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-a812aca62d634905aa95c3de20bc79d7
Source dataset
uspto-grants-2015_06
Patent number
US09050311B2

Reaction notes

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