Hydrochloric Acid → HCID 68809166, compound

HRID 1725331Notes

Reaction equation

HRID 1725331 reaction equation
C([O:3][C:4](=[O:19])[C@H:5]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:6][C:7]([O:9][C@H:10]1[CH2:14][CH2:13][O:12][CH2:11]1)=[O:8])C.[OH-].[Na+].Cl>CCO>[O:12]1[CH2:13][CH2:14][C@H:10]([O:9][C:7]([NH:6][C@H:5]([C:4]([OH:19])=[O:3])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:8])[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68810479HCID 68810479, compound

Product 1

HCID 68809166HCID 68809166, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(((3S)-tetrahydrofuran-3-yloxy)carbonyl)-L-leucine ethyl ester (2.9 g, 11 mmol) in EtOH (100 mL) was added 1M NaOH (33 mL). The mixture was stirred under ice-cooling condition for 3 hours, and then adjusted to pH 3 by the addition of HCl thereto. The solution was concentrated in vacuo, and the residue was extracted with ethyl acetate (100 mL). Then, the organic layer was separated, washed with 1M HCl and saturated aqueous NaCl, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was crystallized from ethyl acetate and hexane to give N-(((3S)-tetrahydrofuran-3-yloxy)carbonyl)-L-leucine (2.6 g, 85%) as colorless crystals.

Workup

  1. temperaturecooling condition for 3 hours
  2. concentrationThe solution was concentrated in vacuo
  3. extractionthe residue was extracted with ethyl acetate (100 mL)
  4. customThen, the organic layer was separated
  5. washwashed with 1M HCl and saturated aqueous NaCl
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-3e4652f18dd44b96b13cfd1a01f5732c
Source dataset
uspto-grants-2009_02
Patent number
US07491705B2

Reaction notes

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