Potassium Sodium Tartrate → HCID 66976332, compound

HRID 1022661Notes

Reaction equation

HRID 1022661 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:18]1[C:24](=O)[CH:23]([OH:26])[CH:22]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[O:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH2:11]([N:18]1[CH2:24][CH:23]([OH:26])[CH:22]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[O:21][CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66975410HCID 66975410, compound

Product 1

HCID 66976332HCID 66976332, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (11.2 g) in THF (120 ml) was added, in an argon stream, aluminum(III) chloride (10.5 g) at room temperature, and the mixture was stirred at room temperature for 40 min. The reaction mixture was cooled to 0° C., a solution of (6RS,7RS)-4-benzyl-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepan-5-one (28.9 g) in THF (100 mL) was added dropwise, and the mixture was stirred for 3 hr. To the reaction mixture was added 10% aqueous Rochelle salt solution (90 mL) at 0° C., and the mixture was stirred at room temperature for 30 min, and filtered through celite. The filtrate was washed with brine, the organic layer was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (27.7 g).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe mixture was stirred for 3 hr
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. filtrationfiltered through celite
  5. washThe filtrate was washed with brine
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ad928a0fdaff4c1e98d7446a34f6804a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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