Acetyl chloride → Methyl N-acetyl-beta-alaninate
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7].[C:9](Cl)(=[O:11])[CH3:10]>>[CH3:2][O:3][C:4](=[O:8])[CH2:5][CH2:6][NH:7][C:9](=[O:11])[CH3:10]Participants
3
Procedure
According to scheme II, β-alanine methyl ester hydrochloride 4 is reacted with acetyl chloride giving N-acetyl-β-alanine methyl ester 5 which is reacted with disulfide cystamine 6 upon heating neat at 80° C. giving the tetraamide disulfide product N, N-(Dithiodi-2,1-ethanediyl bis [3-(acetylamino) propanamide 7. Reductive cleavage of the disulfide bond of 7 with sodium borohydride in methanol gives the unstable thiol 8 which is reacted in situ with an excess of oleoyl chloride 1, giving the thioester product S-[2-[[3-(acetylamino)-1-oxopropyl]amino]ethyl]-9(Z)-octadecenethioate 9. ##STR10##
Sources & evidence
- ORD record
- ord-dc7e3f155cbe4f37bea237213ba5bd2b
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05173510
Reaction notes
Loading…