2-Butenedioic acid, monoethyl ester → (E)-ethyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate

HRID 926912Notes

Reaction equation

HRID 926912 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=O.[C:11]([NH:34][CH2:35][CH2:36][NH:37]C(=O)/C=C/C(OC)=O)(=[O:33])[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH3:32]>>[C:11]([NH:34][CH2:35][CH2:36][NH:37][C:4](=[O:6])/[CH:3]=[CH:2]/[C:1]([O:8][CH2:9][CH3:10])=[O:7])(=[O:33])[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 58782252-Butenedioic acid, monoethyl esterHCID 53255264(E)-methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate

Product 1

HCID 53340288(E)-ethyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate

Procedure

Mono ethyl fumarate (commercially available) was subjected to the same reaction conditions outlined earlier in the preparation of (E)-methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate. The desired product, namely (E)-ethyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z) -docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate, was obtained after purification by silica gel chromatography. MS (EI) calcd for C30H40N2O4: 496.33; found 497 (M+1).

Sources & evidence

ORD record
ord-96a9d6b463e34d2cbe83470155b5656e
Source dataset
uspto-grants-2016_03
Patent number
US09289503B2

Reaction notes

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