Sodium → HCID 13900948, compound

HRID 477646Notes

Reaction equation

HRID 477646 reaction equation
[Na].C[O:3][C:4]([C@H:6]1[C@H:10]([C:11]([O:13]C)=[O:12])[O:9][C:8]([CH:28]([Br:30])[CH3:29])([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[C:21]=3[Br:25])[CH:16]=2)[O:7]1)=[O:5]>O.CO>[Br:30][C@H:28]([C:8]1([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[C:21]=3[Br:25])[CH:16]=2)[O:9][C@@H:10]([C:11]([OH:13])=[O:12])[C@H:6]([C:4]([OH:5])=[O:3])[O:7]1)[CH3:29]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 13595208HCID 13595208, compound

Product 1

HCID 13900948HCID 13900948, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxyde (5.32 g, 0.133 mol) in water (70 ml) was added dropwise in 1 hour, under stirring, to a solution of the diastereoisomer 3 (35.4 g, 0.0665 mol) in methanol (250 ml) at 20° C. The reaction mixture was kept at 20° C. for 2 hours; then methanol was removed under reduced pressure mantaining the initial volume of the solution by addition of water. The aqueous solution, so obtained, was extracted with dichloromethane, acidified with conc HCl to pH 1, and extracted with diethylether (3×100 ml). The combined organic extracts were washed with water, anhydrified over sodium sulfate, filtered, and concentrated in vacuo. Crystallization of the residue from dichloromethane gave the pure 2-(1(S)-bromoethyl)-2-(5-bromo-6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid (diastereoisomer 7).

Workup

  1. customthen methanol was removed under reduced pressure
  2. additionby addition of water
  3. customThe aqueous solution, so obtained
  4. extractionwas extracted with dichloromethane
  5. extractionextracted with diethylether (3×100 ml)
  6. washThe combined organic extracts were washed with water
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization of the residue from dichloromethane

Sources & evidence

ORD record
ord-b424f12692a9493484b26cab29fcf654
Source dataset
uspto-grants-1989_12
Patent number
US04888433

Reaction notes

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