Methyl L-threoninate hydrochloride → N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Threonine

HRID 650785Notes

Reaction equation

HRID 650785 reaction equation
[C:1]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][O:25][P:26]([OH:29])([OH: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].Cl.[CH3:34]OC(=O)[C@H]([C@@H](C)O)N>>[C:1]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[C@@H:24]([CH3:34])[O:25][P:26]([OH:29])([OH: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]

Participants

3

Reactant 2

HCID 2734893Methyl L-threoninate hydrochlorideHCID 86583929N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Serine

Product 1

HCID 86583930N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Threonine

Procedure

This compound was prepared as described above for (6) using 1 mmol (170 mg) of L-threonine methyl ester hydrochloride; yield 97 mg, (40%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 1.2-1.4 (m, 11H, 4CH2 and CH3CHOP); 2.0-2.4 (m, 6H, 2CH2CH═CH and CH2CO); 2.7-2.9 (br s, 6H, 3HC═CHCH2CH═CH); 4.1-4.3 (m, 2H, 2CH); 5.2-5.4 (br s, 8H, 4HC═CH); 8.2-8.4 (m, 3H, NH and 2POH)

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b3b2ef1e85184311b3fed0e0d617a6f5
Source dataset
uspto-grants-2001_08
Patent number
US06274747B1

Reaction notes

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