Hydrochloric Acid → HCID 10112104, compound

HRID 2182923Notes

Reaction equation

HRID 2182923 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]([N:23]3[CH2:26][CH:25]([C:27]([O:29]C)=[O:28])[CH2:24]3)=[O:22])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].Cl>O1CCOCC1.O>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]([N:23]3[CH2:26][CH:25]([C:27]([OH:29])=[O:28])[CH2:24]3)=[O:22])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrate2×HCID 10224048HCID 10224048, compound

Product 1

HCID 10112104HCID 10112104, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 1-[(5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazol-3-yl)carbonyl]-3-azetidinecarboxylate (Example 18) (130 mg, 0.31 mmol) in 1,4-dioxane (3 ml) was cooled to 0° C. and treated with lithium hydroxide monohydrate (25 mg, 0.60 mmol). The mixture was stirred for 1 hour being allowed to warm to room temperature over this time. Further lithium hydroxide monohydrate (25 mg, 0.60 mmol) was added and the mixture stirred for 3 hours. The mixture was then treated with hydrochloric acid (2M), diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by HPLCb to afford the title compound as a foam (110 mg).

Workup

  1. stirringthe mixture stirred for 3 hours
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by HPLCb

Sources & evidence

ORD record
ord-af5ed8091085460da82fa30f08b2a60e
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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