Sodium Hydroxide → HCID 11457378, compound

HRID 1760159Notes

Reaction equation

HRID 1760159 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:26])[CH2:19][C@@H:20]([OH:25])[CH2:21][C:22]([O-:24])=[O:23])=[C:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])[N:11]=2)=[CH:6][CH:5]=1.C[NH3+].S([O-])([O-])(=O)=O.[Mg+2:43]>O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:26])[CH2:19][C@@H:20]([OH:25])[CH2:21][C:22]([O-:24])=[O:23])=[C:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])[N:11]=2)=[CH:6][CH:5]=1.[Mg+2:43].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:26])[CH2:19][C@@H:20]([OH:25])[CH2:21][C:22]([O-:24])=[O:23])=[C:14]([CH:27]([CH3:29])[CH3:28])[N:13]=[C:12]([N:30]([S:31]([CH3:34])(=[O:33])=[O:32])[CH3:35])[N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10185967355805-96-8

Product 1

HCID 11457378HCID 11457378, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
38 °C

Procedure

1.0M Sodium hydroxide solution (26.3 ml) was added to a stirred solution of methylammonium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (15 g) in water (106 ml) at ambient temperature. A solution of magnesium sulphate (4.3 g) in water (26 ml) was added over 20 minutes and a solid precipitated. The solid was collected by filtration, washed with water (20 ml) and dried under vacuum at 40° C. (7.7 g). A mixture of the solid (5.8 g) and water (50 ml) was heated to 38° C. and diluted with water (35 ml). The mixture was stirred at ambient temperature for 4 hours and then allowed to stand for 66 hours. The solid was collected by filtration after diluting with water (30 ml). The product was dried at 35° C. under vacuum to give magnesium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (4.68 g) as white crystals. The X-ray powder diffraction spectra for a typical sample of the crystalline magnesium salt is shown in FIG. 9 hereinafter. The ten most prominent peaks in the XRD occur at about 2-theta=11.5, 14.5, 16.3, 16.8, 18.0, 19.1, 19.8, 21.8, 22.6 and 23.0°.

Workup

  1. customa solid precipitated
  2. filtrationThe solid was collected by filtration
  3. washwashed with water (20 ml)
  4. customdried under vacuum at 40° C. (7.7 g)
  5. additionA mixture of the solid (5.8 g) and water (50 ml)
  6. additiondiluted with water (35 ml)
  7. waitto stand for 66 hours
  8. filtrationThe solid was collected by filtration
  9. additionafter diluting with water (30 ml)
  10. customThe product was dried at 35° C. under vacuum

Sources & evidence

ORD record
ord-2a9ec81fa60e4b05b168ba9a12a53c4f
Source dataset
uspto-grants-2005_01
Patent number
US06841554B2

Reaction notes

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