Hydrochloric Acid → HCID 22627183, compound

HRID 1108737Notes

Reaction equation

HRID 1108737 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])=[C:14]([CH2:26][CH2:27][CH3:28])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:11][CH:10]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C.[OH-].[Na+]>[NH2:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])=[C:14]([CH2:26][CH2:27][CH3:28])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22627494HCID 22627494, compound

Product 1

HCID 22627183HCID 22627183, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 6-tert-butoxycarbonylamino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (581 mg) in ethyl acetate (5 ml) was added 4N hydrogen chloride in ethyl acetate (5 ml) at 20° C. The reaction mixture was stirred at 20° C. for 6.5 hours, then diluted with 1N aqueous sodium hydroxide and extracted. The organic phase was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:6 to 1:4) to give 6-amino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (361 mg) as yellow oil.

Workup

  1. extractionextracted
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:6 to 1:4)

Sources & evidence

ORD record
ord-fcbcc92a9ca74058be05851a16976024
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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