Ethyl Acetate → HCID 118113308, compound

HRID 1485107Notes

Reaction equation

[CH:1]1([C:4]2[CH:21]=[CH:20][C:7]([O:8][C:9]3[CH:14]=[N:13][C:12]([CH:15]4OCC[O:16]4)=[CH:11][N:10]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CC(C)=O>[CH:1]1([C:4]2[CH:21]=[CH:20][C:7]([O:8][C:9]3[N:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution in acetone (107 mL) of the compound (2.46 g) obtained in step (3) above, p-toluenesulfonic acid monohydrate (2.04 g) was added and the mixture was stirred at 50° C. for two hours. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium hydrogencarbonate was added to it under cooling with ice and two extractions were conducted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate; thereafter, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-80:20) to give the titled compound as a colorless solid (0.67 g).

Workup

temperatureAfter cooling the reaction mixture to room temperature
temperatureunder cooling with ice and two extractions
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
customthereafter, the desiccant was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-80:20)

Sources & evidence

ORD record: ord-6be7af2622a44a4e9284ee5960a35880
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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