Hydrochloric Acid → HCID 59497353, compound

HRID 1747473Notes

Reaction equation

HRID 1747473 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[C:20]3=[O:34])[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Li+].Cl>O1CCOCC1.O.C(OCC)(=O)C>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][NH:8]2)=[C:12]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:20]2=[O:34])[CH:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59497231HCID 59497231, compound

Product 1

HCID 59497353HCID 59497353, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-4-[3-(2-methoxycarbonyl-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-indole-1-carboxylic acid tert-butyl ester 270 mg (0.56 mmol) is taken up in dioxane 4 mL and then the lithium hydroxide 53 mg 2.23 mmol in water is added to the solution. The reaction is stirred for 2 hours and then made acidic by the addition of 1N HCl. The compound is then extracted into ethyl acetate and then the ethyl acetate is dried (MgSO4) filtered and evaporated in vacuo. The oil is taken up in dichloromethane and TFA is added. The reaction is stirred for 1 hour and then evaporated in vacuo to give a solid that is taken up in ethyl acetate and precipitated with hexanes. The solid is collected and washed with hexanes to give the title compound (156 mg, 0.42 mmol, 76%). LCMS (ESMS): m/z 370.8 (M+H+).

Workup

  1. extractionThe compound is then extracted into ethyl acetate
  2. dry with materialthe ethyl acetate is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionTFA is added
  6. stirringThe reaction is stirred for 1 hour
  7. customevaporated in vacuo
  8. customto give a solid
  9. customprecipitated with hexanes
  10. customThe solid is collected
  11. washwashed with hexanes

Sources & evidence

ORD record
ord-40a3a842fbcf4d8cbebe43e57ac49899
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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