Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 57545029, compound

HRID 2355492Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([NH:24][CH2:25][CH:26]([N:35](C)[C:36](OCC[Si](C)(C)C)=O)[CH2:27][C:28]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.[N+](CC)(CC)(CC)CC.[F-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([NH:24][CH2:25][CH:26]([NH:35][CH3:36])[CH2:27][C:28]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (3R)-3-((S)-1-(3-fluorophenyl)-1-hydroxy-5-methoxypentyl)-N-(3-(1-hydroxycyclohexyl)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)piperidine-1-carboxamide (9.7 mg, 0.015 mmol) in anhydrous THF (1 mL) was added Et4NF (3 mg). The solution was stirred at 45° C. for 2 h and evaporated under reduced pressure. The residue was purified by prep HPLC to give (3R)-3-((S)-1-(3-fluorophenyl)-1-hydroxy-5-methoxypentyl)-N-(3-(1-hydroxycyclohexyl)-2-(methylamino)propyl)piperidine-1-carboxamide (4.5 mg, 50%) as its TFA salt. 1H NMR (400 MHz, CD3OD): 7.32 (t, 1H), 7.16 (d, 1H), 7.14 (d, 1H), 6.94 (td, 1H), 4.36 (t, 1H), 3.88 (t, 1H), 3.53 (m, 1H), 3.40 (m, 1H), 3.26 (s, 3H), 2.61 (s, 3H), 2.48 (m, 1H), 2.47 (m, 1H), 1.94 (t, 2H), 1.90 (td, 1H), 1.76 (tt, 1H), 1.69-1.22 (m, 18H), 0.99 (m, 1H); MS m/z 524 (M+H+).

Workup

customevaporated under reduced pressure
customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-897bb17dc0ee4d9998c51532d73138b7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754737B2

Reaction notes

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