Ammonia → Methyl 2-carbamoyl-3-[4-[2-(2-naphthoxy)ethoxy]phenyl]propionate

HRID 458723Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[CH:12][CH:11]=1)[C:6](O)=[O:7])=[O:4].S(Cl)(Cl)=O.[NH3:34]>C1C=CC=CC=1.C(OCC)(=O)C>[C:6]([CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])(=[O:7])[NH2:34]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(methoxycarbonyl)-3-[4-[2-(2-naphthoxy)ethoxy]phenyl]propionic acid (2.08 g, 5.29 mmol) in benzene (20 ml) at room temperature is added thionyl chloride (0.76 g, 6.34 mmol). Then the mixture was heated at 80° C. for 90 min. After cooled to room temperature, the solvent is removed under a vacuum. To the residue is added 28% ammonia solution (5.49 ml, 79.30 mmol) at room temperature. The mixture is stirred for 30 min, dissolved in ethyl acetate (20 ml), washed with brine (3×15 ml), dried over sodium sulfate, and concentrated. The crude product is crystallized from ethanol to give title compound (0.98 g, 47%). HRMS calcd for C23H23NO5: 393.4364. Found: 393.4363. MA calcd for C23H23NO5: C, 70.22%; H, 5.89%; N, 3.56%. Found: C, 70.54%; H, 5.87%; N, 3.54%.

Workup

temperatureAfter cooled to room temperature
customthe solvent is removed under a vacuum
washwashed with brine (3×15 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude product is crystallized from ethanol

Sources & evidence

ORD record: ord-ffec458d79644f04a859b99050ef3654
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192970B2

Reaction notes

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