Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → (3R)-N-((S)-3-cyclohexyl-1-(methylamino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamide

HRID 1254379Notes

Reaction equation

HRID 1254379 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C@:30]([OH:43])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:25]2)=[S:23])[CH2:9][N:10](C)[C:11](OCC[Si](C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](CC)(CC)(CC)CC.[F-]>CC#N>[CH:1]1([CH2:7][C@H:8]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C@:30]([OH:43])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:25]2)=[S:23])[CH2:9][NH:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 86626199(3R)-N-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamide

Product 1

HCID 57544614(3R)-N-((S)-3-cyclohexyl-1-(methylamino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamideYield 25.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3R)-N-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamide (35 mg, 52 μmol) and Et4NF (40 mg, 0.26 mmol) in MeCN (1 mL) was heated at 60° C. in a microwave for 10 min. The reaction mixture was submitted directly to prep HPLC to afford (3R)-N-((S)-3-cyclohexyl-1-(methylamino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamide (6.4 mg, 23%) and recovered (3R)-N-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbothioamide (11.2 mg).

Sources & evidence

ORD record
ord-c4b1ff9a8d274480918dccd2cb9b3678
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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