Hydrochloric Acid → HCID 59497426, compound

HRID 1747467Notes

Reaction equation

HRID 1747467 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:27]3[O:26][C:25](=[O:28])[NH:24][C:23]=3[CH:22]=[C:21]([Cl:29])[CH:20]=2)[C:10]1=[O:30])[CH2:6][CH2:7][CH3:8].[OH-].[Li+].Cl>O1CCOCC1>[Cl:29][C:21]1[CH:20]=[C:19]([CH2:18][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:9]([CH:5]([CH2:6][CH2:7][CH3:8])[CH2:4][C:3]([OH:31])=[O:2])[C:10]2=[O:30])[C:27]2[O:26][C:25](=[O:28])[NH:24][C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59497418HCID 59497418, compound

Product 1

HCID 59497426HCID 59497426, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[3-(5-Chloro-2-oxo-2,3-dihydro-benzooxazol-7-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid methyl ester (40 mg 0.08 mmol) is dissolved in 750 μL of 1,4 dioxane and then lithium hydroxide (5 mg in 750 μL of water) is added to the reaction. The reaction is stirred at room temperature for 1 hour and then acidified with 1N HCl. The product is extracted with ethyl acetate 3×1 mL) and the combined organic layers are dried, filtered and evaporated in vacuo. The crude material is purified by preparative reverse phase LC to give the title compound 20 mg (0.04 mmol, 54%). LCMS (ESMS): m/z 430.8 (M+H+).

Workup

  1. extractionThe product is extracted with ethyl acetate 3×1 mL) and the combined organic layers
  2. customare dried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude material is purified by preparative reverse phase LC

Sources & evidence

ORD record
ord-016cfbb7652a4cb4ab6e8b72c11b25e2
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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