Lithium Hydroxide → HCID 66756932, compound

HRID 855819Notes

Reaction equation

HRID 855819 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:25]([CH2:26][CH3:27])[CH2:24][CH2:23][C@H:17]1[C:18]([O:20]CC)=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:25]([CH2:26][CH3:27])[CH2:24][CH2:23][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66756585HCID 66756585, compound

Product 1

HCID 66756932HCID 66756932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(tert-butoxycarbonyl)-L-leucyl-(5S)-5-ethyl-L-prolinate (0.965 g, 2.5 mmol) was dissolved in 3 mL of ethanol. The resultant solution was treated with 1.2 M LiOH solution (3.8 mL, 4.52 mmol) at room temperature. After 4 hours, the volatiles were removed under reduced pressure, and 1 N HCl was added. The mixture was extracted with ethyl acetate (3×), and the combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound. MS (ESI) m/z 357 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure, and 1 N HCl
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61463bf50a0040fea94287d830f4086b
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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