Sodium potassium tartrate tetrahydrate → HCID 66975631, compound

HRID 1022570Notes

Reaction equation

HRID 1022570 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([N:18]1[CH2:24][CH:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:22]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([F:41])[CH:35]=2)[O:21][CH2:20][C:19]1=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:11]([N:18]1[CH2:24][CH:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:22]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([F:41])[CH:35]=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 2724148Sodium potassium tartrate tetrahydrateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66975364HCID 66975364, compound

Product 1

HCID 66975631HCID 66975631, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of aluminum(III) chloride (5.28 g) in THF (396 mL) was added, under a nitrogen stream, lithium aluminum hydride (4.51 g) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added dropwise a solution of (6RS,7SR)-4-benzyl-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-3-one (31.5 g) in THF (264 ml), and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added aqueous potassium sodium (+)-tartrate tetrahydrate (93.0 g) solution at 0° C., and the mixture was stirred at room temperature overnight, and filtered through celite. The obtained oil was diluted with ethyl acetate, and the mixture was washed with distilled water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (26.4 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 0° C. for 2 hr
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationfiltered through celite
  5. additionThe obtained oil was diluted with ethyl acetate
  6. washthe mixture was washed with distilled water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8cf7172d80fc4309aec8a27e2cb2bed6
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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