Hydrochloric Acid → (2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid 4-allyl-2-methoxy-phenyl ester

HRID 82494

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(N(C(C)C)C(C)C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:44]1([O:54][CH3:55])[C:45](=[CH:47][CH:48]=[C:49]([CH:53]=1)[CH2:50][CH:51]=[CH2:52])O>ClCCl.CN(C1C=CN=CC=1)C>[CH2:50]([C:49]1[CH:48]=[CH:47][C:45]([O:9][C:8](=[O:10])[CH2:7][CH:5]2[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]2)=[C:44]([O:54][CH3:55])[CH:53]=1)[CH:51]=[CH2:52]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid (30.0 g, 0.17 mol) in dichloromethane (300 mL) were added N-ethyldiisopropyl amine (147 mL, 0.86 mol), EDCI. HCl (98.0 g, 0.51 mol), HOBt (13.1 g, 0.08 mol), DMAP (0.2 g, 0.01 mol) at ice temperature (0° C.) and the reaction mixture was stirred at same temperature over a period of 15 min. Then eugenol (26.1 mL, 0.17 mol) was added to the reaction mixture at same temperature and the mixture was stirred at room temperature (25° C.) over a period of 5 h. The resulting mixture was diluted with dichloromethane (2.0 L), washed with water (4×500 mL), dried (Na2SO4) and concentrated. The residue obtained upon evaporation of the solvent was washed with petroleum ether to obtain product as a off-white solid (35.0 g, 63%).

Workup

washwashed with water (4×500 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue obtained upon evaporation of the solvent
washwas washed with petroleum ether

Sources & evidence

ORD record: ord-23e30c064a8c441fbbe52fe158a0e70c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846721B2

Linked notes

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