Sodium Hydroxide → HCID 66976421, compound

HRID 1022562Notes

Reaction equation

HRID 1022562 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]([F:40])=[C:36]([Cl: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.[OH-].[Na+]>C(OCC)C.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]([F:40])=[C:36]([Cl: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

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66975041HCID 66975041, compound

Product 1

HCID 66976421HCID 66976421, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum(III) chloride (1.12 g) in diethyl ether (85 mL)-THF (40 mL) was added, under a nitrogen stream, lithium aluminum hydride (960 mg) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C., a solution of (6RS,7SR)-4-benzyl-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3-chloro-4-fluorophenyl)-1,4-oxazepan-3-one (6.72 g) in THF (60 mL) was added dropwise, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added 1 N aqueous sodium hydroxide solution (14 ml) at −78° C., the mixture was stirred at room temperature for 2 hr, and filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (4.16 g).

Workup

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

Sources & evidence

ORD record
ord-ef5768c1d5be4e9884e754d26985ed79
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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