Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 16752763, compound

HRID 253605

Reaction equation

HRID 253605 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[O:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([OH:46])[CH2:34][N:35](C)[C:36](OCC[Si](C)(C)C)=O)[CH2:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[N+](CC)(CC)(CC)CC.[F-]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[O:22][CH2:21][CH2:20][N:19]([C:23](=[O:47])[NH:24][C@H:25]([C@H:33]([OH:46])[CH2:34][NH:35][CH3:36])[CH2:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 66861750HCID 66861750, compound

Product 1

HCID 16752763HCID 16752763, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 10 mL flask was charged with methyl 2-((S)-(3-chlorophenyl)((R)-4-((2S,3R)-3-hydroxy-4-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamoyl)morpholin-2-yl)methoxy)ethylcarbamate (30 mg, 0.043 mmol) dissolved in MeCN (4 mL) and Et4NF (14 mg, 0.094 mmol) was added. The mixture was stirred for 0.5 h under reflux. After stirring, it was monitored by HPLC until the reaction ended. The solution was concentrated in vacuo and purified by HPLC to give the target compound (2.97 mg, 12%). 1H NMR (MeOD) 1.27-1.30 (m, 2H), 1.32-1.40 (m, 2H), 1.51-1.62 (m, 2H), 1.65-1.80 (m, 2H), 2.70 (s, 3H), 1.75-1.90 (m, 2H), 1.90-3.10 (m, 4H), 3.65 (s, 3H), 3.80-3.95 (m, 5H), 4.05-4.20 (m, 1H), 4.30 (m, 1H), 7.25-7.40 (m, 4H).

Workup

  1. temperatureunder reflux
  2. stirringAfter stirring
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-30caf40a8ac34126bfc62f556e4938bb
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Linked notes

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