4,7,10,13,16,19-cis-Docosahexaenoic acid → N-(cis4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-2-Aminoethanol

HRID 2185841Notes

Reaction equation

HRID 2185841 reaction equation
[C:1]([NH:22][CH2:23][CH2:24][O:25][P:26](=[O:28])=[O:27])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:29](O)(=O)[CH2:30]C/C=C\CC=CCC=CCC=CCC=CCC=CCC>>[C:1]([NH:22][CH2:23][CH2:24][O:25][P:26](=[O:28])=[O:27])(=[O:21])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:29][CH3:30]

Participants

3

Reactant 2

HCID 730132534,7,10,13,16,19-cis-Docosahexaenoic acidHCID 86583926N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-2-Aminoethanol

Product 1

HCID 86583927N-(cis4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-2-Aminoethanol

Procedure

This compound was prepared as described above for (5), using 0.5 mmol (164 mg) of cis-4,7,10,13,16,19-docosahexaenoic acid; yield 99 mg (44%); Rf 0.10-0.15 (system B); 1H NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 2.0-2.1 (t, 2H, CH2CO); 2.2-2.4 (m, 4H, 2CH2CH═CH); 2.7-2.9 (br s, 10H, 5HC═CHCH2CH═CH); 3.4-3.5 (br s, 2H, CH2NH); 3.9-4.0 (br s, 2H, CH2OP); 5.2-5.4 (br s, 12H, 6HC═CH); 8.2-8.4 (m, 3H, NH and 2POH).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-09bb6663bc934f4e8094a4e631bd4549
Source dataset
uspto-grants-2002_06
Patent number
US06403554B2

Reaction notes

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