Hydrochloric Acid → HCID 10595053, compound

HRID 1069651Notes

Reaction equation

HRID 1069651 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][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:13]=[C:12]2[CH2:25][C:26]([NH2:28])=[O:27])C.[OH-].[Na+].Cl>CCO.C1COCC1>[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][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10548672HCID 10548672, compound

Product 1

HCID 10595053HCID 10595053, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[[3-(2-Amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester (260 mg, 0.66 mmol) was stirred with 2 mL of 2N NaOH in 25 mL of EtOH and 5 mL of THF for 18 hours. The mixture was acidified with 5N HCl, extracted with EtOAc, the EtOAc solution washed with saturated NaCl solution and dried (Na2SO4). After concentrating, the residue was crystallized from methylene chloride/ethanol to give 110 mg (46% yield) of 4-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid, mp, 160-163° C.

Workup

  1. extractionextracted with EtOAc
  2. washthe EtOAc solution washed with saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationAfter concentrating
  5. customthe residue was crystallized from methylene chloride/ethanol

Sources & evidence

ORD record
ord-0eee161ef09241a89183e864d89975ab
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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