Lithium Hydroxide → HCID 59444214, compound

HRID 1888123Notes

Reaction equation

HRID 1888123 reaction equation
[CH3:1][CH:2]([CH3:19])[C@@H:3]([CH2:8][NH:9][C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1>[CH3:1][CH:2]([CH3:19])[C@@H:3]([CH2:8][NH:9][C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:16])[CH3:17])=[O:11])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59444289HCID 59444289, compound

Product 1

HCID 59444214HCID 59444214, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 3-methyl-2-(((2-(trimethylsilyl)ethoxy)carbonylamino)methyl)butanoate (459 mg, 1.586 mmol) in THF (4 mL) was added 2 M LiOH (4.0 mL, 8.00 mmol). Upon completion of addition, the mixture was stirred at rt for 20 hrs. After this time, the reaction mixture was quenched with sat'd NH4Cl (about 4 ml) and then 1 N HCl (8 ml) was added. The crude product was extracted with EtOAc and the extract was washed with brine. The combined aqueous layers were back extracted with EtOAc. The EtOAc extracts were combined, dried over Na2SO4 and evaporated to give the title compound as an oily residue, which was used in the next step without further purification.

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the reaction mixture was quenched with sat'd NH4Cl (about 4 ml)
  3. addition1 N HCl (8 ml) was added
  4. extractionThe crude product was extracted with EtOAc
  5. washthe extract was washed with brine
  6. extractionThe combined aqueous layers were back extracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-25cbe06377f3492fbd01417ee7251c79
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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