Lithium Hydroxide → HCID 22895005, compound

HRID 322696Notes

Reaction equation

HRID 322696 reaction equation
C([O:3][C:4](=[O:24])[C@H:5]([CH3:23])[NH:6][C:7](=[O:22])[C@H:8]([CH3:21])[NH:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)C.[Li+].[OH-]>O1CCOCC1.O>[F:18][C:16]1[CH:17]=[C:12]([CH2:11][C:10]([NH:9][C@H:8]([C:7]([NH:6][C@H:5]([C:4]([OH:24])=[O:3])[CH3:23])=[O:22])[CH3:21])=[O:20])[CH:13]=[C:14]([F:19])[CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10154430HCID 10154430, compound

Product 1

HCID 22895005HCID 22895005, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by dissolving 1.98 g (0.006 mols) of N-[N-(3,5-difluorophenylacetyl)-L-alaninyl]-L-alanine ethyl ester (from Example 85 below) in 60 mL dioxane and A 15 mL of H2O and adding LiOH (0.25 g, 0.006 mol) that has been dissolved in 15 mL of H2O. After stirring for 3 hours, the dioxane was removed under reduced pressure and the residue diluted with EtOAc, the layers were separated and the aqueous layer acidified to pH 2. The aqueous layer was back extracted with EtOAc (4×100 ml), and the combined organics were dried over Na2SO4 and the solvent was removed under reduced pressure after filtration. The residue was recrystallized from EtOAc/isooctane giving 1.7 g (90%). C14H16F2N2O4 requires C, 53.50 H, 5.13 N, 8.91. Anal found C, 53.30 H, 5.26 N, 8.98.

Workup

  1. customthe dioxane was removed under reduced pressure
  2. additionthe residue diluted with EtOAc
  3. customthe layers were separated
  4. extractionThe aqueous layer was back extracted with EtOAc (4×100 ml)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. filtrationafter filtration
  8. customThe residue was recrystallized from EtOAc/isooctane giving 1.7 g (90%)

Sources & evidence

ORD record
ord-20651c2e522d4fa6a932851308417884
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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