3-(((benzyloxy)carbonyl)amino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate → 3-amino-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate

HRID 1770709Notes

Reaction equation

HRID 1770709 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(OC([NH:22][C:23]([CH3:39])([CH3:38])[CH2:24][CH2:25][N+:26]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:28])[CH3:27])=O)C1C=CC=CC=1>[Pd].CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[NH2:22][C:23]([CH3:38])([CH3:39])[CH2:24][CH2:25][N+:26]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 866655243-(((benzyloxy)carbonyl)amino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate

Product 1

HCID 866655253-amino-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 10% palladium on carbon (200 mg) was added to a solution of 3-(((benzyloxy)carbonyl)amino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate (0.95 g, 1.7 mmol) in 7 mL of methanol. The flask was degassed and placed under a hydrogen atmosphere, stirring for 18 hours at room temperature. The suspension was filtered through a pad of celite, washing with methanol, and the filtrate was concentrated under reduced pressure to give 725 mg of clear viscous oil (quantitative yield). 1H NMR (400 MHz, D2O) δ 0.75-78 (t, J=6.4 Hz, 3H), 1.09 (s, 6H), 1.7-1.26 (m, 6H), 1.47-1.51 (m, 2H), 1.80-1.84 (m, 2H), 2.30 (s, 3H), 3.03 (s, 6H), 3.36-3.40 (m, 2H), 3.44-3.48 (m, 4H), 3.81 (br s, 2H), 7.27-7.28 (d, J=8.1 Hz, 2H), 7.58-7.60 (d, J=8.1 Hz, 2H). LRMS (ESI/APCI) m/z 259 [M]+.

Workup

  1. customThe flask was degassed
  2. filtrationThe suspension was filtered through a pad of celite
  3. washwashing with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a5022dcd9694923a71620bd1d86502c
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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