Hydrochloric Acid → HCID 25052188, compound

HRID 73356Notes

Reaction equation

HRID 73356 reaction equation
C([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])[CH:18]=3)[C:13]([C:34]#[N:35])=[CH:12]2)=[CH:7][C:6]=1[O:36]COC)C.C(O)C.O.[OH-].[Li+].Cl>O.O1CCCC1>[CH2:27]([O:26][C:24]([NH:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[C:19]2[C:14]([C:13]([C:34]#[N:35])=[CH:12][N:11]2[C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:40])=[O:3])=[C:6]([OH:36])[CH:7]=2)=[CH:15][CH:16]=1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 584372394-[6-(2-Benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxy-benzoic acid ethyl ester

Product 1

HCID 25052188HCID 25052188, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[6-(2-benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxybenzoic acid ethyl ester (0.14 g) in a mixed solvent of ethanol (2.5 mL), tetrahydrofuran (5 mL), and water (2.5 mL) was added lithium hydroxide mono hydrate (0.03 g), and this mixture was stirred at room temperature for 3 hours. To this reaction mixture was added 2 mol/L hydrochloric acid (0.75 mL), and this mixture was stirred at 50° C. for 5 hours. This reaction mixture was treated 1 mol/L hydrochloric acid (5 mL), and this mixture was concentrated under reduced pressure until this solvent volume became one-third. The precipitated solid was collected by filtration, and washed with water, methanol and ether to give the title compound (0.097 g)

Workup

  1. stirringthis mixture was stirred at 50° C. for 5 hours
  2. concentrationthis mixture was concentrated under reduced pressure until this solvent volume
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water, methanol and ether

Sources & evidence

ORD record
ord-c69f05d65d344809817f7a2d846e89b4
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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