Hydrochloric Acid → Raltegravir

HRID 1023682Notes

Reaction equation

HRID 1023682 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]([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+].Cl>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]([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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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

Product 1

HCID 54671008RaltegravirYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Raltegravir potassium (˜3.4 g) in water was acidified with 2N HCl until pH 2 was obtained. The acidified solution was extracted with mixture of methyl tert-butyl ether (MTBE)/isopropyl alcohol (IPA) (400 ml/100 ml). The organic extract was evaporated to dryness. Raltegravir free hydroxy (3.1 g) was obtained as a white powder.

Workup

  1. customwas obtained
  2. extractionThe acidified solution was extracted with mixture of methyl tert-butyl ether (MTBE)/isopropyl alcohol (IPA) (400 ml/100 ml)
  3. extractionThe organic extract
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-e62f058f5185464aa178bf975f4c4aa7
Source dataset
uspto-grants-2014_05
Patent number
US08722722B2

Reaction notes

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