Palmitoyl chloride → 3-Hexadecanamidocyclohexanone

HRID 1592840ノート

反応式

HRID 1592840 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1.[C:9](Cl)(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[C:9]([NH:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1)(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

3

反応物 2

HCID 8206Palmitoyl chlorideHCID 218731843-Aminocyclohexan-1-one

生成物 1

HCID 218731823-Hexadecanamidocyclohexanone

実験手順

2-Cyclohexenone is reacted with benzylamine to give 3-benzylaminocyclohexanone. Hydrogenolysis of the benzylamino group then gives 3-aminocyclohexanone. Reaction with hexadecanoyl chloride affords 3-hexadecanamidocyclohexanone, which is then reduced with sodium borohydride to produce a cis/trans mixture of 3-hexadecanamidocyclohexanol. Separation by column chromatography then gives the pure isomers. Reaction with bromoethylphosphodichloridate, then with trimethylamine will produce 3-hexadecanamido-cyclohexylphosphocholine.

出典と根拠

ORDレコード
ord-34486c3e38074f4d85f96fbe6405a9e7
出典データセット
uspto-grants-2007_11
特許番号
US07294619B2

反応ノート

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