Hydrochloric Acid → HCID 15551858, compound

HRID 1069605Notes

Reaction equation

HRID 1069605 reaction equation
C([O:3][C:4](=[O:33])[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][CH2:23]CCCC)[C:13]([CH3:28])=[C:12]2[CH2:29][C:30]([NH2:32])=[O:31])C.[OH-].[Na+].O.Cl>CO>[NH2:32][C:30](=[O:31])[CH2:29][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:3])=[O:33])[CH:10]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:13]=1[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 10647569HCID 10647569, compound

Product 1

HCID 15551858HCID 15551858, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 190 mg (0.46 mmol) of [4-[[3-(2-amino-2-oxoethyl)-1-decyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester and 2 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 precipitate was filtered and recrystallized from MeOH. There was obtained 50 mg (28% yield) of [4-[[3-(2-amino-2-oxoethyl)-1-cyclohexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid. mp, 212-214° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 2.5 hours
  4. temperaturecooled
  5. filtrationThe precipitate was filtered
  6. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-659790511f4247b1bf99ec37c29e0179
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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