Potassium Hydroxide → Warfarin Potassium

HRID 1618099Notes

Reaction equation

HRID 1618099 reaction equation
[CH3:1][C:2]([CH2:4][CH:5]([C:12]1[C:21](=[O:22])[O:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]=1[OH:23])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3].[K].[OH-].[K+:26].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C([N-]C(C)C)(C)C.[K+]>O.C([O-])([O-])=O.[K+].[K+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[CH3:1][C:2]([CH2:4][CH:5]([C:12]1[C:21](=[O:22])[O:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O-:23])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3].[K+:26]

Participants

9

Reactant 5

HCID 14797Potassium Hydroxide4×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 5462222PotassiumHCID 11073506Potassium diisopropylamideHCID 54678486Warfarin

Product 1

HCID 23706212Warfarin Potassium

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 11430Potassium CarbonateSolvent4×HCID 62657Potassium Phosphate, TribasicSolvent4×

Procedure

Illustrative embodiments of the present invention provide a process for preparing APO-II comprising: i. mixing Warfarin acid in isopropanol thereby forming a Warfarin mixture; ii. adding to the Warfarin mixture a potassium base selected from either ii-i) KOH, K2CO3, KHCO3, K3PO4, KOH in water, K2CO3 in water, KHCO3 in water, K3PO4 in water, KOH in ROH, K2CO3 in ROH, KHCO3 in ROH, K3PO4 in ROH, and mixtures thereof, wherein R is selected from the group consisting of H and C1-C4 alkyl, or ii-ii) KOH, K2CO3, KHCO3, K3PO4, KH, KNH2, potassium bis(trimethylsilyl)amide, potassium diisopropylamide and mixtures thereof, thereby forming a potassium Warfarin mixture; iii. heating the potassium Warfarin mixture to a temperature in a range of from about 45° C. to about 80° C. thereby forming a first solution; iv. maintaining the first solution at a pH in a range of from about 7.0 to about 10.0 thereby forming a Warfarin potassium isopropanol solution; v. distilling the Warfarin potassium isopropanol solution thereby forming a concentrated Warfarin potassium isopropanol solution; vi. adding additional isopropanol to the concentrated Warfarin potassium isopropanol solution and distilling further to remove water thereby forming a distilled Warfarin potassium isopropanol solution; vii. distilling the distilled Warfarin potassium isopropanol solution to dryness or near-dryness thereby forming a Warfarin potassium residue; viii. dissolving the Warfarin potassium residue in ethyl acetate thereby forming a Warfarin potassium ethyl acetate solution; ix. stirring the Warfarin potassium ethyl acetate solution at a temperature in a range of from about 5° C. to about 50° C. until precipitation occurs thereby forming a precipitate; and x. isolating the precipitate thereby isolating APO-II.

Sources & evidence

ORD record
ord-b248ee5b1e9344699802cdcf23ccf4a0
Source dataset
uspto-grants-2014_07
Patent number
US08765976B2

Reaction notes

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