Hydrochloric Acid → HCID 10303884, compound

HRID 1760158Notes

Reaction equation

HRID 1760158 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.[Na+].Cl.[Cl-].[Na+]>C(#N)C>[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.[CH2:8]([NH3+:9])[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 23684378sodium (3R,5S,6E)-7-(4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate

Product 1

HCID 10303884HCID 10303884, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

A solution of sodium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate in aqueous acetonitrile (40 ml) was cooled to −5° C. and 1M hydrochloric acid (9.5 ml) containing sodium chloride (7.1 g) was added to adjusted the pH to 3.8. The aqueous phase was separated off and acetonitrile (70 ml) was added to the organic phase. Benzylamine (1.4 ml) was added and the solution was heated to 30° C. and held at this temperature for 90 minutes. The product was isolated by filtration at 0° C. and dried at 35° C. under vacuum to give benzylammonium (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate (4.4 g) as white crystals. The X-ray powder diffraction spectra for a typical sample of the crystalline benzylammonium salt is shown in FIG. 6 hereinafter. The ten most prominent peaks in the XRD occur at about 2-theta=6.1, 6.7, 16.8, 17.6, 18.1, 19.3, 21.1, 21.9, 23.0 and 26.8°.

Workup

  1. additionwas added
  2. customThe aqueous phase was separated off
  3. additionacetonitrile (70 ml) was added to the organic phase
  4. additionBenzylamine (1.4 ml) was added
  5. customThe product was isolated by filtration at 0° C.
  6. customdried at 35° C. under vacuum

Sources & evidence

ORD record
ord-e07902b540134f8190921b24f9392cb1
Source dataset
uspto-grants-2005_01
Patent number
US06841554B2

Reaction notes

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