Potassium Hydroxide → 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 1023667Notes

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]>CCO.O>[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

Conditions

Temperature: 50 °C

Procedure

A vial (20 ml) was charged with Raltegravir free hydroxy (200 mg) slurry in EtOH:H2O (1000:1, 0.2 ml) at room temperature. The slurry was heated to 50° C. A solution of 45% aqueous KOH (0.044 ml) was added at 50° C. to the mixture. The resulting mixture was stirred for 5.5 h at 50° C. To this mixture was added distilled H2O (1.5 ml) dropwise to produce a colorless solution. The solvent was then removed under reduced pressure to provide wet Raltegravir potassium crystalline Form VI. The product was dried in a vacuum oven at 40° C. for 3.5 hours to provide Raltegravir potassium crystalline Form VI.

Workup

additionTo this mixture was added
distillationdistilled H2O (1.5 ml) dropwise
customto produce a colorless solution
customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record: ord-8b662a9313324e57bc606751f3d7be7b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722722B2

Reaction notes

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