Lithium Hydroxide → HCID 22895005, compound

HRID 1016873Notes

Reaction equation

HRID 1016873 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 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-39df07dcd3134ce4b3366cfc3d62dd37
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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