Lithium Hydroxide → N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-ethynyl-L-proline

HRID 475337Notes

Reaction equation

HRID 475337 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:24]([C:25]#[C:26][Si](C)(C)C)[CH2:23][CH2:22][C@H:17]1[C:18]([O:20]C)=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCOCC1.Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:24]([C:25]#[CH:26])[CH2:23][CH2:22][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66757129methyl N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

Product 1

HCID 71367827N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-ethynyl-L-proline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-((trimethylsilyl)ethynyl)-L-prolinate (1.24 g, 2.83 mmol) in dioxane (12 mL) at room temperature was added a solution of 2 M lithium hydroxide (3 mL, 6.0 mmol). The resulting mixture was stirred at room temperature for 6 hours. The reaction was diluted with 1 M HCl solution (50 mL), and the aqueous mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated to provide the titled compound.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cef1eb08a698461b98e66d88a7e7cedb
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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