Hydrochloric Acid → HCID 10117701, compound

HRID 1760156Notes

Reaction equation

HRID 1760156 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C@@H:16]([OH:24])[CH2:17][C@@H:18]([OH:23])[CH2:19][C:20]([O-:22])=[O:21])=[C:12]([CH:25]([CH3:27])[CH3:26])[N:11]=[C:10]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])[N:9]=2)=[CH:4][CH:3]=1.C[NH3+:35].C(OCC)(=O)C.Cl.O>[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C@@H:16]([OH:24])[CH2:17][C@@H:18]([OH:23])[CH2:19][C:20]([O-:22])=[O:21])=[C:12]([CH:25]([CH3:27])[CH3:26])[N:11]=[C:10]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])[N:9]=2)=[CH:4][CH:3]=1.[NH4+:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 10185967355805-96-8

Product 1

HCID 10117701HCID 10117701, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
5 °C

Procedure

Methylammonium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (10 g) was added to ethyl acetate (125 ml). The mixture was cooled to 5° C. and 1M hydrochloric acid in saturated brine (20 ml) was added, followed by water (30 ml) to obtain a two-phase solution. The aqueous phase was separated off and the organic phase was washed with water (30 ml) and dried over anhydrous magnesium sulphate. Aqueous ammonia (1.7 ml) was added, followed by ethyl acetate (80 ml), and the solution was concentrated under vacuum and diluted with ethyl acetate (60 ml). The mixture was stirred at 0° C. to 5° C. for 90 minutes and the product was isolated by filtration and dried at 30° C. under vacuum to give ammonium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (6.33 g) as white crystals. The X-ray powder diffraction spectra for a typical sample of the crystalline ammonium salt is shown in FIG. 1 hereinafter. The ten most prominent peaks in the XRD occur at about 2-theta=12.9, 15.2, 18.0, 18.2, 18.5, 20.2, 22.4, 23.0, 24.0 and 27.2°.

Workup

  1. customto obtain a two-phase solution
  2. customThe aqueous phase was separated off
  3. washthe organic phase was washed with water (30 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. additionAqueous ammonia (1.7 ml) was added
  6. concentrationthe solution was concentrated under vacuum
  7. additiondiluted with ethyl acetate (60 ml)
  8. customthe product was isolated by filtration
  9. customdried at 30° C. under vacuum

Sources & evidence

ORD record
ord-053cdaefbe28472ca434822a70c96c98
Source dataset
uspto-grants-2005_01
Patent number
US06841554B2

Reaction notes

Loading…