L-Tartaric acid → HCID 22042229, compound

HRID 434521Notes

Reaction equation

HRID 434521 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].FC1C=CC(C2(O)ONC(CN3CCC(N4C5C=CC(Cl)=CC=5NC4=O)CC3)=C2O)=CC=1>C(O)C.O>[OH2:3].[C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 20492819HCID 20492819, compound

Product 1

HCID 22042229HCID 22042229, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 46.5 g-quantity of the above compound (free base) is dissolved in 200 ml of ethanol, and a solution of 15 g of L-tartaric acid in 200 ml of water is added to the ethanol solution. The resulting mixture is allowed to stand at room temperature. The crystals thus precipitated are recrystallized three times from ethanol-water (6:4) to give tartrate monohydrate as colorless prisms. The tartrate monohydrate is treated with an aqueous solution of sodium bicarbonate to give (-)-1-[5-(4-fluorophenyl)-4,5-dihydroisoxazol-3-ylmethyl]-4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine. Melting point: 143°-145° C. [α]D25 : -108.8 (chloroform).

Workup

  1. customto stand at room temperature
  2. customThe crystals thus precipitated
  3. customare recrystallized three times from ethanol-water (6:4)

Sources & evidence

ORD record
ord-87d9b87514c64c7ab521664c05549dda
Source dataset
uspto-grants-1983_08
Patent number
US04397853

Reaction notes

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