Lithium Hydroxide → Strontium ranelate octahydrate

HRID 468581Notes

Reaction equation

HRID 468581 reaction equation
[O:1]1[CH2:5][CH2:4]CC1.C([O:8][C:9]([C:11]1[S:12][C:13]([NH:23][CH:24]([C:30]([O:32]CC)=[O:31])C(OCC)=O)=[C:14]([C:21]#[N:22])[C:15]=1[CH2:16][C:17]([O:19]C)=[O:18])=[O:10])C.[OH-:35].[Li+].[Cl-].[Sr+2:38].[Cl-]>O>[CH2:16]([C:17]([O-:19])=[O:18])[C:15]1[C:14]([C:21]#[N:22])=[C:13]([N:23]([CH2:24][C:30]([O-:32])=[O:31])[CH2:4][C:5]([O-:1])=[O:35])[S:12][C:11]=1[C:9]([O-:8])=[O:10].[OH2:1].[OH2:1].[OH2:1].[OH2:1].[OH2:1].[OH2:1].[OH2:1].[OH2:1].[Sr+2:38].[Sr+2:38]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 536248510476-85-4HCID 68933746HCID 68933746, compound

Product 1

HCID 71300750Strontium ranelate octahydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tetrahydrofuran (375 ml), 5-(bis-ethoxycarbonylmethyl-amino)-4-cyano-3-methoxycarbonylmethyl-thiophene-2-carboxylic acid ethyl ester (250 g) and 1200 ml 10% aq. solution of lithium hydroxide was stirred at room temperature for about 4 to 6 hours in a round bottom flask. The reaction mass was filtered off to remove any insoluble material. The clear filtrate was further stirred with 2.2 moles of strontium chloride in 1.7 liters of water for 15 to 20 hours at room temperature. The precipitated solid, distrontium salt of 2-[N-N-di(carboxymethyl-)amino]-3-cyano-4-carboxymethylthiophene-5-carboxylic acid in the form of an octahydrate, was filtered off and washed with water to form a wet cake. The resulting wet cake was dried to yield 333 grams of strontium ranelate octahydrate having a purity greater than 99.5% as determined by HPLC.

Workup

  1. filtrationThe reaction mass was filtered off
  2. customto remove any insoluble material
  3. filtrationThe precipitated solid, distrontium salt of 2-[N-N-di(carboxymethyl-)amino]-3-cyano-4-carboxymethylthiophene-5-carboxylic acid in the form of an octahydrate, was filtered off
  4. washwashed with water
  5. customto form a wet cake
  6. customThe resulting wet cake was dried

Sources & evidence

ORD record
ord-9252861ff87c445a8c4db6b765b17215
Source dataset
uspto-grants-2014_01
Patent number
US08624041B2

Reaction notes

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