Triethylamine → HCID 72195415, compound
Reaction equation
[C:1]([OH:24])(=O)[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]\[CH2:21][CH3:22].CCN=C=[N:29][CH2:30][CH2:31][CH2:32]N(C)C.C1C=CC2N([OH:45])N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[OH:45][CH2:32][CH2:31][CH2:30][NH:29][C:1](=[O:24])[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]\[CH2:21][CH3:22]Participants
6
Procedure
To a solution of (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (3.3 g, 10 mmol) in 50 mL of anhydrous CH2Cl2 were added EDCI (2.2 g, 11.0 mmol), HOBt (1.5 g, 11.0 mmol), and Et3N at 0° C. The reaction mixture was allowed to warm to room temperature, and stirred overnight. The reaction mixture was diluted with 50 mL of CH2Cl2 and washed successively with water (3×20 mL), brine (30 mL). The resulting organic layer was dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by column chromatography (gradient elution from 2:1 pentane/EtOAc to 1:2 pentane/EtOAc) to afford 3.0 g of (4Z,7Z,10Z,13Z,16Z,19Z)—N-(3-hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide (78% yield).
Workup
- washwashed successively with water (3×20 mL), brine (30 mL)
- dry with materialThe resulting organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (gradient elution from 2:1 pentane/EtOAc to 1:2 pentane/EtOAc)
Sources & evidence
- ORD record
- ord-1c4ec94f973a4e9ebbf1c10e62b7a1e9
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150504B2
Reaction notes
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