Triethylamine → HCID 71478041, compound

HRID 527165Notes

Reaction equation

HRID 527165 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12].[OH:15][C:16]12[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:28])[C:20]1([NH:29][C:30](=[O:32])[CH3:31])[C:19]1[CH:33]=[CH:34][C:35]([CH:37]([CH3:39])[CH3:38])=[CH:36][C:18]=1[O:17]2>C1COCC1>[C:8]([O:17][C:18]1[CH:36]=[C:35]([CH:37]([CH3:38])[CH3:39])[CH:34]=[CH:33][C:19]=1[C:20]1([NH:29][C:30](=[O:32])[CH3:31])[C:21](=[O:28])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]1=[O:15])(=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 86716885HCID 86716885, compound

Product 1

HCID 71478041HCID 71478041, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.24 ml, 1.77 mmol) and Valeroyl chloride (0.18 ml, 1.48 mmol) were added to N-(4b-hydroxy-7-isopropyl-10-oxo-9b,10-dihydro-4bH-benzo[d]indeno[1,2-b]furan-9b-yl)acetamide (0.50 g, 1.48 mmol) in THF (10 ml). The reaction mixture was stirred at room temperature for 12 hrs, concentrated in a vacuum to remove solvent. The reaction mixture was extracted with water and methylene chloride, and purified through silica gel column chromatography (ethylacetate:hexane=1:2) to afford the title compound (0.20 g, 32%).

Workup

  1. concentrationconcentrated in a vacuum
  2. customto remove solvent
  3. extractionThe reaction mixture was extracted with water and methylene chloride
  4. custompurified through silica gel column chromatography (ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-edffe43a86064ca484f508d993ae9c79
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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