Ethyl 4-oxobutanoate → 4-[N-dodecyl-N-2-[4-iodophenoxy]ethylamino]butanoic acid, ethyl ester

HRID 1383910Notes

Reaction equation

[I:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].O=[CH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CO.C(OCC)(=O)C>[CH2:10]([N:9]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:8][CH2:7][O:6][C:5]1[CH:22]=[CH:23][C:2]([I:1])=[CH:3][CH:4]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 22 °C

Procedure

To a mixture of N-2-[4-iodophenoxy]ethyldodecylamine ( 4.0 g, 9.3 mmol) and sodium cyanoborohydride (1.45 g, 23 mmol) in methanol (80 ml) was added dropwise a solution of ethyl 4-oxobutyrate (Fournet, G. ; Balme, G.; Barieux, J. J. and Gore, J. Tetrahedron, 1988, 44, 5821) (2.4 g, 18 mmol) in methanol (20 ml) over a period of 10 min. The resulting mixture was stirred at 22° C. for 24 h, and then diluted with ethyl acetate (600 ml), washed with brine (3×250 ml). The aqueous phase was extracted with ethyl acetate (150 ml), and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (Hexane/ethyl acetate 8:1 to 6:1) to afford the title compound (4.5 g, 89%) as a colorless oil.

Workup

washwashed with brine (3×250 ml)
extractionThe aqueous phase was extracted with ethyl acetate (150 ml)
dry with materialthe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (Hexane/ethyl acetate 8:1 to 6:1)

Sources & evidence

ORD record: ord-e5fea5b26ca14b5caae909f62ed46e01
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255496B1

Reaction notes

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