Octanoyl chloride → HCID 90097582, compound

HRID 527150Notes

Reaction equation

HRID 527150 reaction equation
[NH2:1][C:2]12[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:3]1([OH:22])[O:4][C:5]1[C:10]2=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1.C(N([CH2:28][CH3:29])CC)C.[C:30](Cl)(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[CH:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2]1([NH:1][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:20](=[O:21])[C:19]3[C:14]([C:3]1([O:22][C:3](=[O:4])[CH2:2][CH2:10][CH2:9][CH2:8][CH2:7][CH2:28][CH3:29])[O:4]2)=[CH:15][CH:16]=[CH:17][CH:18]=3)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 86716884HCID 86716884, compound

Product 1

HCID 90097582HCID 90097582, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9b-amino-4b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride (10 ml) was added triethylamine (0.20 g, 2.01 mmol) and octanoyl chloride (0.27 g, 1.67 mmol) and then stirred for 28 hrs. The reaction mixture was concented and extracted with ethylacetate. The concentrated organic layer was purified using silica gel column chromatography (ethylacetate:hexane=1:6 to 1:4) to afford the title compound as a syrup (55 mg, 15%).

Workup

  1. extractionextracted with ethylacetate
  2. customThe concentrated organic layer was purified

Sources & evidence

ORD record
ord-e2a9f9d8949442748b01fd101727782f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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