Hydrochloric Acid → sodium (3R,5S,6E)-7-(4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate

HRID 39407Notes

Reaction equation

HRID 39407 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]3[O:21]C(C)(C)[O:19][C@@H:18]([CH2:24][C:25]([O:27]C(C)(C)CC4C=CC=CC=4)=[O:26])[CH2:17]3)=[C:12]([CH:38]([CH3:40])[CH3:39])[N:11]=[C:10]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:44])=[O:43])[N:9]=2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+:49]>O1CCCC1>[Na+:49].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C@@H:16]([OH:21])[CH2:17][C@@H:18]([OH:19])[CH2:24][C:25]([O-:27])=[O:26])=[C:12]([CH:38]([CH3:40])[CH3:39])[N:11]=[C:10]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:44])=[O:43])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49854668HCID 49854668, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (15.38 g) prepared in Example 19 was dissolved in tetrahydrofuran (80 ml) and a 0.1M hydrochloric acid aqueous solution (19.21 ml) was added thereto, followed by stirring for 24 hours while heating to 40° C. The reaction liquid was cooled to room temperature and a 0.5M sodium hydroxide aqueous solution (81 ml) was added thereto over 5 minutes, followed by stirring for 4 hours. Ethyl acetate (250 ml) and purified water (250 ml) were added to the reaction liquid, and the organic layer was separated, washed with saturated sodium chloride (150 ml), dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to give (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid sodium salt.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. waitover 5 minutes
  4. stirringby stirring for 4 hours
  5. customEthyl acetate (250 ml) and purified water (250 ml)
  6. additionwere added to the reaction liquid
  7. customthe organic layer was separated
  8. washwashed with saturated sodium chloride (150 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb56204e32a243b6be53fa8dd09abb80
Source dataset
uspto-grants-2013_09
Patent number
US08524914B2

Reaction notes

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