Water → HCID 11270506, compound

HRID 1787377Notes

Reaction equation

HRID 1787377 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]3[C:17]([CH3:24])=[C:18]([NH2:23])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:26])[CH3:25])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[C:27]([CH2:31][C:32](Cl)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C.O>ClCCl>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]3[C:17]([CH3:24])=[C:18]([NH:23][C:32](=[O:33])[CH2:31][C:27]([CH3:30])([CH3:29])[CH3:28])[C:19]([CH3:22])=[C:20]([CH3:21])[C:15]=3[O:14][C:13]2([CH3:26])[CH3:25])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 68710214HCID 68710214, compound

Product 1

HCID 11270506HCID 11270506, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-tert-butylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine hydrochloride obtained in Reference Example 76 (400 mg, 1.16 mmol) and tert-butylacetyl chloride (0.17 mL, 1.22 mmol) in dichloromethane (10 mL) was added triethylamine (0.35 mL, 2.50 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with 1 N hydrochloric acid and an aqueous saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain 110 mg (yield: 41%) of the title compound. Amorphous substance.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with 1 N hydrochloric acid
  4. dry with materialan aqueous saturated sodium hydrogen carbonate solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-e260cacfcc8646cc9b5ae0ac5ee2fa82
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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