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

HRID 1770708Notes

Reaction equation

HRID 1770708 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]([CH3:18])([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=[O:29])=[O:28])=[CH:23][CH:22]=1>>[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1.[CH2:1]([O:8][C:9]([NH:10][C:11]([CH3:12])([CH3:18])[CH2:13][CH2:14][N+:15]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH3:16])[CH3:17])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 132797162-(Hexyloxy)ethyl 4-methylbenzenesulfonateHCID 60134454Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate

Product 1

HCID 866655243-(((benzyloxy)carbonyl)amino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonateYield 64%

Conditions

Temperature
75 °C

Procedure

A mixture of benzyl(4-(dimethylamino)-2-methylbutan-2-yl)carbamate (0.72 g, 2.7 mmol) and 2-(hexyloxy)ethyl 4-methylbenzenesulfonate (1.8 g, 6.0 mmol) was stirred overnight at 75° C. The crude reaction mixture was purified by reverse phase HPLC eluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid) to give 0.96 g of white solid (64% yield). 1H NMR (400 MHz, D2O) δ 0.75-78 (m, 3H), 1.18 (s, 6H), 1.44-1.27 (m, 2H), 2.06 (br m, 2H), 2.29 (s, 3H), 3.03 (s, 6H), 3.17-3.21 (m, 2H), 3.30 (br m, 2H), 3.36-3.39 (t, J=6.5 Hz, 2H), 3.67 (br s, 2H), 4.97 (br s, 2H), 7.26-7.28 (d, J=8.1 Hz, 2H), 7.30-7.37 (m, 5H), 7.58-7.60 (d, J=8.1 Hz, 2H). LRMS (ESI/APCI) m/z 393 [M]+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by reverse phase HPLC
  3. washeluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid)

Sources & evidence

ORD record
ord-0af8062f9f2443d2a281fca87a327472
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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