Lithium hydroxide, monohydrate → N-(tert-Butoxycarbonyl)-N-(2-methylpropyl)glycine

HRID 1927795Notes

Reaction equation

HRID 1927795 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:7]([CH3:9])[CH3:8].O.[OH-].[Li+]>C1COCC1.O.C(OCC)(=O)C>[C:13]([O:12][C:10]([N:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:4][C:3]([OH:17])=[O:2])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86640544HCID 86640544, compound

Product 1

HCID 23033833N-(tert-Butoxycarbonyl)-N-(2-methylpropyl)glycineYield 40%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Nα-(tert-Butyloxycarbonyl)-Nα-(2-methylpropyl) glycine methyl ester (960 mg, 3.91 mmol) was dissolved in THF/H2O (9:1, 25 ml). Lithium hydroxide monohydrate (492 mg, 11.7 mmol) was added. After 18 h at room temperature the reaction mixture was diluted with ethyl acetate (100 ml). This solution was washed with 1M HCl, water and brine, dried (Na2SO4) and evaporated in vacuo to give a colourless oil identified as the title compound (360 mg, 1.56 mmol, 40%).

Workup

  1. washThis solution was washed with 1M HCl, water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-75521753ec454662b01760bae0fc4f55
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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