Sodium Iodide → HCID 18472642, compound

HRID 2228295Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([C:17]([O:19][CH3:20])=[O:18])[CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH3:20][O:19][C:17]([C:4]1[CH:3]=[C:2]([N:1]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:16]=[CH:15][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of ethyl 4-(4-amino-2-methoxycarbonyl-phenoxy)butyrate (2.20 g), bis(2-chloroethyl)ether (0.915 ml, 7.81 mmol), potassium carbonate(3.24 g, 23.4 mmol), sodium iodide (2.34 g, 15.6 mmol) and DMF (20 ml) was stirred at 70° C. for 24 hours, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 30 g,.ethyl acetate/hexane=1/4), and the desired fraction was concentrated under reduced pressure to give ethyl 4-(2-methoxycarbonyl-4-morpholinophenoxy)butyrate (2.18 g). IR (KBr): 1732 cm−1.

Workup

concentrationthe mixture was concentrated under reduced pressure
additionTo the residue was added water
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified with column chromatography (silica gel 30 g,.ethyl acetate/hexane=1/4)
concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0d1d9799b0a1497fbf90d7ce413db5fa
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413947B1

Reaction notes

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