Trifluoroacetic acid → N~1~,N~4~-Bis(4-aminobutyl)benzene-1,4-dicarboxamide

HRID 1716265Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:34])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)=[CH:16][CH:15]=1)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:34])=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68676006HCID 68676006, compound

Product 1

HCID 68675849N~1~,N~4~-Bis(4-aminobutyl)benzene-1,4-dicarboxamide

Procedure

{4-[4-(4-tert-Butoxycarbonylamino-butylcarbamoyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester (0.49 g) is treated with neat TFA (5 mL) and allowed to stand at RT overnight. The acid is removed in vacuo to afford the title compound as a yellow solid. Alternatively, deprotection can be carried out using 33% HBr is acetic acid. [M+H]+ 307.22

Workup

customThe acid is removed in vacuo

Sources & evidence

ORD record: ord-292b19b5b8224ee2897f5ad68e374199
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803804B2

Reaction notes

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