Hydrochloric Acid → HCID 86718239, compound

HRID 2401649Notes

Reaction equation

HRID 2401649 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C@@H:19]([C:24]([O:26]C)=[O:25])[CH2:20][CH2:21][CH2:22][CH3:23])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Li+].[ClH:35]>C1COCC1.CO>[ClH:35].[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH2:21][CH2:22][CH3:23])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86718184HCID 86718184, compound

Product 1

HCID 86718239HCID 86718239, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

890 mg of methyl N-({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)-D-norleucinate Example 19 (2 mmol, 1 equivalent) were dissolved in 16 ml of THF/methanol (1:1), 10 ml of 1 N aqueous lithium hydroxide solution (10 mmol, 5 equivalents) were added and the mixture was stirred at 45° C. for 2 h. With ice cooling, the mixture was then adjusted to pH 5-6 using 6 N aqueous hydrochloric acid, and the organic solvent was removed under reduced pressure. A little water was added to the residue, and the mixture was extracted repeatedly with dichloromethane/methanol=100:5. The combined organic phases were dried over magnesium sulphate, filtered and concentrated. The residue obtained was dried under high vacuum. This gave 844 mg (95% of theory; purity: 98%) of the title compound.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. additionA little water was added to the residue
  3. extractionthe mixture was extracted repeatedly with dichloromethane/methanol=100:5
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas dried under high vacuum

Sources & evidence

ORD record
ord-72916db1201c40f682a151c09522d366
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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