Hydrochloric Acid → 4-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid

HRID 1069598Notes

Reaction equation

HRID 1069598 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([CH3:24])=[C:12]2[CH2:25][C:26]([NH2:28])=[O:27])C.[OH-].[Na+].O.Cl>CO>[NH2:28][C:26](=[O:27])[CH2:25][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:29])=[O:3])[CH:10]=2)[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]=1[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86757072HCID 86757072, compound

Product 1

HCID 155518574-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acidYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 170 mg (0.42 mmol) of [4-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester and 1 mL of 5N NaOH in 20 mL of MeOH was heated to maintain reflux for 2.5 hours, cooled, poured into water and made strongly acidic with 5N HCl. The mixture was extracted with ethyl acetate, dried (Na2SO4), concentrated at reduced pressure and the residue crystallized from MeOH. There was obtained 37 mg (24% yield) of [4-[[3-(2-amino-2-oxoethyl)-1-hexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid. mp, 169-170° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 2.5 hours
  4. temperaturecooled
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated at reduced pressure
  8. customthe residue crystallized from MeOH

Sources & evidence

ORD record
ord-99e124e9337e41d18e262a9a09906bb1
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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