Lithium Hydroxide → HCID 57947353, compound

HRID 409840Notes

Reaction equation

HRID 409840 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:13](=[O:22])[C:12]([CH3:24])([CH3:23])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[OH-:26]>C1COCC1.O>[C:18]([O:17][C:15]([NH:14][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH2:11][C:12]([CH3:24])([CH3:23])[C:13]([OH:26])=[O:22])=[O:16])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57947696HCID 57947696, compound

Product 1

HCID 57947353HCID 57947353, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-3,3-dimethyl-2-oxopyrrolidine-1-carboxylate (2.7 g, 7.56 mmol) in THF (27 mL) and water (3 mL) was added LiOH (1 N, 15.2 mL, 15.2 mmol). The reaction mixture was stirred at RT overnight and concentrated. The residue was dissolved in water (20 mL), acidified with 10% citric acid to pH 6-7, and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to give (S)-4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)-2,2-dimethylpentanoic acid (2.6 g, 91.7%), which was used without further purification. LRMS (M−Boc+H+) m/z 276.2.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water (20 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f19965810cd643cebe3ee57e8c644558
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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