Hydrochloric Acid → HCID 10621578, compound

HRID 1069593Notes

Reaction equation

HRID 1069593 reaction equation
[Al]([NH2:4])(C)C.C1C=CC=CC=1.C([O:13][C:14](=O)[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]([S:35][CH3:36])=[C:22]2[CH2:37][C:38]([NH2:40])=[O:39])C.Cl>C1C=CC=CC=1>[NH2:4][C:14](=[O:13])[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]([S:35][CH3:36])=[C:22]2[CH2:37][C:38]([NH2:40])=[O:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10622985HCID 10622985, compoundHCID 131720268HCID 131720268, compound

Product 1

HCID 10621578HCID 10621578, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

Ten mL of 0.6M (CH3)2AlNH2/benzene was added to 200 mg (0.45 mmol) of 4-[[3-(2-amino-2-oxoethyl)-2-methylthio-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester (Example 46) in 25 mL of benzene and the mixture heated at 50° C. for 1.75 hours. After cooling the mixture was decomposed with ice and 1N HCl added, The mixture was extracted with EtOAc, the EtOAc solution washed with saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was crystallized from EtOH/CH2Cl2 to give 155 mg (84% yield) of 5-(4-amino-4-oxobutoxy)-2-(methylthio)-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 185° C.

Workup

  1. temperatureAfter cooling the mixture
  2. additionadded
  3. extractionThe mixture was extracted with EtOAc
  4. washthe EtOAc solution washed with saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was crystallized from EtOH/CH2Cl2

Sources & evidence

ORD record
ord-eaf7e885668a405a82411eacea3313b7
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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