Hydrochloric Acid → HCID 131720267, compound

HRID 2292791Notes

Reaction equation

HRID 2292791 reaction equation
[Al]([NH2:4])(C)C.C1C=CC=CC=1.C(O[C:14](=[O:41])[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:20]1[C:19]([O:18][CH2:17][CH2:16][CH2:15][CH:14]=[O:41])=[CH:27][CH:26]=[C:25]2[C:21]=1[C:22]([CH2:37][C:38]([NH2:40])=[O:39])=[C:23]([S:35][CH3:36])[N:24]2[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

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

Product 1

HCID 131720267HCID 131720267, 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-oxobutoxyl-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-05cbea27debf439b931fbdd42d91a4ab
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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