Trifluoroacetic acid → (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide

HRID 85372Notes

Reaction equation

[CH3:1][N:2]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[C:3](=[O:25])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:28][CH2:27][CH2:26][N:2]([CH3:1])[C:3](=[O:25])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)—N-methyldocosa-4,7,10,13,16,19-hexaenamido)ethylcarbamate (1.71 g, 3.5 mmol)) in dichloromethane (50 mL) at 0° C. was slowly added TFA (17 mL). The mixture was stirred (0° C., 2 h) basified to pH 10 with saturated aqueous Na2CO3 and extracted with EtOAc (3×150 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to afford (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide (1.31 g, 97%) as a light yellow oil.

Workup

customat 0° C.
extractionextracted with EtOAc (3×150 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3c4f368e25524761a3ad62fa5ce85efc
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846972B2

Reaction notes

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