Acetone → Potassium 4-[{[(4-fluorophenyl)methyl]imino}(hydroxy)methyl]-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl}-6-oxo-1,6-dihydropyrimidin-5-olate

HRID 1752276Notes

Reaction equation

HRID 1752276 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([OH:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[OH-].[K+:34].CC(C)=O.O>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[N:19]([CH3:20])[C:17](=[O:18])[C:16]([O-:21])=[C:15]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])[N:14]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[K+:34]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14797Potassium HydroxideHCID 54671008Raltegravir

Product 1

HCID 23668479Potassium 4-[{[(4-fluorophenyl)methyl]imino}(hydroxy)methyl]-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl}-6-oxo-1,6-dihydropyrimidin-5-olate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrated crystalline form 2 is prepared by sonicating a mixture of raltegravir, KOH, acetone and trace amount of water whereas anhydrous crystalline form 3 is obtained by crystallization of amorphous raltegravir potassium from ethanol.

Workup

  1. customHydrated crystalline form 2 is prepared
  2. customby sonicating

Sources & evidence

ORD record
ord-0ab43a7fbc0742b4aa9b3d5b3a578e5c
Source dataset
uspto-grants-2015_10
Patent number
US09163009B2

Reaction notes

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