Triethylamine → HCID 71477749, compound

HRID 527151Notes

Reaction equation

HRID 527151 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:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C(Cl)Cl>[C:30]([NH:1][C:2]1([C:10]2[CH:9]=[CH:8][C:7]([CH:11]([CH3:12])[CH3:13])=[CH:6][C:5]=2[O:4][C:3](=[O:4])[CH2:2][CH2:10][CH2:9][CH2:28][CH3:29])[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:3]1=[O:22])(=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 86716884HCID 86716884, compound

Product 1

HCID 71477749HCID 71477749, compoundYield 85%

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 hexanoyl chloride (0.22 g, 1.69 mmol) and then stirred for 5 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 (0.14 g, 46%).

Workup

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

Sources & evidence

ORD record
ord-ac970eda0ad0483d84b1fec548945d2c
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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