Trifluoroacetic acid → HCID 71470362, compound

HRID 1424561Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]#[C:10][C:11]2[CH:12]=[C:13]([NH:29][C:30](=[O:52])[C@@H:31]([NH:44]C(=O)OC(C)(C)C)[CH2:32][CH2:33][CH2:34][CH2:35][NH:36]C(=O)OC(C)(C)C)[CH:14]=[C:15]([C:17]#[C:18][C:19]3[C:24]([F:25])=[C:23]([F:26])[N:22]=[C:21]([F:27])[C:20]=3[F:28])[CH:16]=2)[C:5]([F:53])=[C:4]([F:54])[N:3]=1.FC(F)(F)C(O)=O>>[NH2:44][C@@H:31]([CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[C:30]([NH:29][C:13]1[CH:12]=[C:11]([C:10]#[C:9][C:6]2[C:5]([F:53])=[C:4]([F:54])[N:3]=[C:2]([F:1])[C:7]=2[F:8])[CH:16]=[C:15]([C:17]#[C:18][C:19]2[C:20]([F:28])=[C:21]([F:27])[N:22]=[C:23]([F:26])[C:24]=2[F:25])[CH:14]=1)=[O:52]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86673528HCID 86673528, compound

Product 1

HCID 71470362HCID 71470362, compound

Procedure

(S)-di-tert-butyl (6-((3,5-bis((perfluoropyridin-4-yl)ethynyl)phenyl)amino)-6-oxohexane-1,5-diyl)dicarbamate (0.02 g, 0.04 mmol) was reacted with neat trifluoroacetic acid (TFA) (2 mL) and the solution was stirred for 4 hours at room temperature. TFA was evaporated and the product (25 mg, 96%) was purified by recrystallization with ethanol: 1H-NMR (400 MHz, CD3OD) δ 8.08 (d, J=1.3 Hz, 2H), 7.66 (t, J=1.3 Hz, 1H), 4.10 (t, J=6.5 Hz, 1H), 2.96 (t, J=15.3 Hz, 2H), 1.94-2.10 (m, 2H), 1.73 (m, 2H), 1.57 (m, 2H), 1.30 (m, 2H).

Workup

customTFA was evaporated
customthe product (25 mg, 96%) was purified by recrystallization with ethanol

Sources & evidence

ORD record: ord-112d03b67d21474e9b996dfe755262a1
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927728B2

Reaction notes

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