Aspirin → HCID 70345089, compound

HRID 342712Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)(=[O:3])[CH3:2].C([N:16]([CH2:19][CH3:20])[CH2:17]C)C.ClC(OCC)=O.[CH3:27][C:28]1([CH3:35])[O:32]C(CN)C[O:29]1>ClCCl.O>[CH3:27][C:28]1([CH3:35])[O:32][CH:19]([N:16]([CH3:17])[C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C:1](=[O:3])[CH3:2])[CH2:20][O:29]1

Participants

Conditions

Temperature: 0 °C

Procedure

The solution from 2-acetoxybenzoic acid (216 mg, 1.2 mmol) in dichloromethane (4 ml) is treated with triethylamine (0.15 ml, 1.2 mmol), cooled to 0° C., treated dropwise with ethyl chloroformate (0.144 ml, 1.0 mmol), stirred at 0° C. for 2 h and filtered. The filtrate is added at room temperature to a solution of 2,2-dimethyl-4-aminomethyl-1,3-dioxolane (293 mg, 1.0 mmol) and triethylamine (0.14 ml) in dichloromethane (4 ml). After 4 h, water (10 ml) is added and the mixture is stirred. The organic phase is washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and water, dried over magnesium sulphate and concentrated. The residue is purified by column chromatography on silica gel 60 (gradient hexane/ethyl acetate=3/1→1/1). Yield: 143 mg.

Workup

filtrationfiltered
waitAfter 4 h
stirringthe mixture is stirred
washThe organic phase is washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and water
dry with materialdried over magnesium sulphate
concentrationconcentrated
customThe residue is purified by column chromatography on silica gel 60 (gradient hexane/ethyl acetate=3/1→1/1)

Sources & evidence

ORD record: ord-064ea014797745dd91de2ff86659b7de
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859053

Reaction notes

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