Sodium Hydroxide → HCID 18360725, compound

HRID 382327Notes

Reaction equation

HRID 382327 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][C:20](OCC)=[O:21])[CH:14]=2)[NH:9][CH:8]=1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18360749HCID 18360749, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18360725HCID 18360725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.2 g of the compound obtained in Step A in 50 ml of anhydrous THF is added dropwise to a suspension of 1.42 g of lithium aluminum hydride in 50 ml of anhydrous THF cooled in an ice-bath. After stirring for 30 minutes at room temperature, a solution of 5% sodium hydroxide is added dropwise until the evolution of gas ceases. The precipitate that forms is filtered off, the organic phase is evaporated and the residue is taken up in 70 ml of ethyl acetate. The organic phase is washed with water until neutrality, dried over magnesium sulphate and evaporated in vacuo to yield the title product in the form of an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationThe precipitate that forms is filtered off
  3. customthe organic phase is evaporated
  4. washThe organic phase is washed with water until neutrality
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-adbf551d3c884c32aac0966738df292e
Source dataset
uspto-grants-2001_10
Patent number
US06310074B1

Reaction notes

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