Lithium Hydroxide → HCID 89666915, compound

HRID 2171266Notes

Reaction equation

HRID 2171266 reaction equation
[OH-].[Li+].[N+](C1C=CC(C([O:12][CH:13]([CH:24]([CH3:26])[CH3:25])[C@@H:14]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:15])=O)=CC=1)([O-])=O>CO>[OH:12][CH:13]([CH:24]([CH3:26])[CH3:25])[C@@H:14]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH3:15]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89666913HCID 89666913, compound

Product 1

HCID 89666915HCID 89666915, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M lithium hydroxide aqueous solution (30 ml) was added to an MeOH (10 ml) solution containing (2S)-2-((tert-butoxycarbonyl)amino)-4-methylpentan-3-yl 4-nitrobenzoate (10 g) obtained in the 3rd step, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, followed by extraction with ethyl acetate. The organic layers were washed with a saturated sodium hydrogen carbonate aqueous solution and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. Yellow oily matter of tert-butyl ((2S)-3-hydroxy-4-methylpentan-2-yl)carbamate (5.3 g) was thus obtained.

Workup

  1. customobtained in the 3rd step
  2. distillationThe solvent was distilled away under reduced pressure
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layers were washed with a saturated sodium hydrogen carbonate aqueous solution and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-49fa492fd1ab46b092ee94bd9854b846
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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