Lithium Hydroxide → HCID 57947353, compound

HRID 340978Notes

Reaction equation

HRID 340978 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-0b91badad051477fbe39f6ac94e7cd4f
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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