Acetic Acid → HCID 66653131, compound

HRID 1681672Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].ClC(O[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.Cl.[C:17]([OH:20])(=[O:19])C>>[C:17]([NH:3][CH2:2][CH2:1][NH:4][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:20])=[O:19]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 3301Ethylenediamine

HCID 10387Benzyl chloroformate

Product 1

HCID 66653131HCID 66653131, compound

Procedure

According to scheme VIII, ethylenediamine is first treated with an excess of benzyl chloroformate followed by mono-hydrolysis using hydrochloric acid in glacial acetic acid giving N-carboxybenzylethylenediamine 25 which is treated with N-acetyl-β-alanine methyl ester 5, giving the protected carbamate [2-[[-(acetylamino)-1-oxopropyl]amino]ethyl]carbamic acid, phenylmethyl ester 26 which is deprotected using palladium on carbon in refluxing ethanol/cyclohexane, giving amine 3-(acetylamino)-N-(2-aminoethyl)propanamide 27. Amine 27 is reacted with oleoyl chloride 1 to give the amide isostere product N-[2-[[3-(acetylamino)-1-oxopropyl]amino]ethyl]-9(Z)-octadecenamide 28. ##STR16##

Sources & evidence

ORD record: ord-c9fd16d6116a49b6840a5995267ae620
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05173510

Reaction notes

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