Water → HCID 23114017, compound

HRID 2376287Notes

Reaction equation

HRID 2376287 reaction equation
[NH2:1][C:2]1[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[C:13]=1[CH3:14].[C:17]([CH2:21][C:22](Cl)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.O>ClCCl>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:21][C:22]([NH:1][C:2]1[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]2[O:9][C:8]([CH3:10])([CH3:11])[C:7](=[O:12])[C:6]=2[C:13]=1[CH3:14])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 23114216HCID 23114216, compound

Product 1

HCID 23114017HCID 23114017, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2,2,4,6,7-pentamethyl-1-benzofuran-3 (2H)-one obtained in Reference Example 57 (3.00 g, 13.7 mmol) and tert-butylacetyl chloride (2.03 g, 15.1 mmol) in dichloromethane (30 mL) was added triethylamine (2.3 mL, 16.4 mmol) at room temperature, and the mixture was stirred at room temperature for 30 minutes. Water was added to the residue to separate the organic layer, and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with 1 N hydrochloric acid and a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the targeted product 2.34 g (yield 54%). Melting point: 155-156° C.

Workup

  1. customto separate the organic layer
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed with 1 N hydrochloric acid
  4. dry with materiala saturated sodium hydrogen carbonate solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4cf0bdba205f47cf965329b48b0c2928
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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