Trifluoroacetic acid → N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate

HRID 1349400Notes

Reaction equation

[C:1]1([C@H:7]([OH:26])[CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18]C(OC(C)(C)C)=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[C:1]1([C@H:7]([OH:26])[CH2:8][NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-(2-phenyl-2-(S)-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline (2.5 g, 7.0 mmole) in CH2Cl2 (15 mL) was cooled in an ice bath under stream of nitrogen and TFA (15 mL) was slowly added. The reaction mixture was stirred for 2 h at 0° C. and then concentrated in vacuo. The crude product was dissolved in 20% MeCN/H2O and purified by preparative reversed phase HPLC (5 to 2% MeCN/H2O over 50 min; 254 nm: 20 mL/min.), to give N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate salt 31 as a colorless oil. 1H-NMR (CD)3OD, 299.96 MHz): δ (ppm); 7.45–7.25 (m, 9H), 4.9 (dd, 1H). 3.55–3.45 (m, 2H), 3.21–3.15 (t, 2H), 3.05–2.95 (t, 2H) ESMS (C16H20N2O1): calcd. 256.4, obsd. 257.1 [M+H]+, 280.2 [M+Na]−.

Workup

additionwas slowly added
concentrationconcentrated in vacuo
dissolutionThe crude product was dissolved in 20% MeCN/H2O
custompurified by preparative reversed phase HPLC (5 to 2% MeCN/H2O over 50 min; 254 nm: 20 mL/min.)

Sources & evidence

ORD record: ord-1caf8951889e42d4a5c48fab193f66c7
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211695B2

Reaction notes

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