Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate → 3-(((Benzyloxy)carbonyl)amino)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate

HRID 1770704Notes

Reaction equation

HRID 1770704 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:7])[CH3:6].CO[CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[C:35]([S:37]([O-:40])(=[O:39])=[O:38])[CH:34]=[CH:33][C:32]=1[CH3:41]>>[CH3:41][C:32]1[CH:33]=[CH:34][C:35]([S:37]([O-:40])(=[O:39])=[O:38])=[CH:36][CH:31]=1.[CH2:11]([O:10][C:9]([NH:8][C:5]([CH3:7])([CH3:6])[CH2:4][CH2:3][N+:2]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])([CH3:1])[CH3:19])=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 60134454Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamateHCID 1317319672-[2-(2-Methoxyethoxy)ethoxy]ethoxy-p-toluenesulfonate

Product 1

HCID 866655193-(((Benzyloxy)carbonyl)amino)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonateYield 115%

Conditions

Temperature
45 °C

Procedure

A mixture of benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate (0.54 g, 2 mmol) and [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]p-toluenesulfonate (1.3 g, 4 mmol) was stirred overnight at 45° C. The crude reaction mixture was directly purified by reverse phase HPLC eluting from a C18 column with a gradient of 5 to 95% acetonitrile in water (with 0.01% acetic acid) to give a clear oil (0.95 g, 2.3 mmol). 1H NMR (D2O, 400 MHz) δ 1.18 (s, 6H), 2.05 (br m, 2H), 2.29 (s, 3H), 2.86 (s, 6H), 3.17-3.21 (m, 2H), 3.26 (s, 3H), 3.30 (br s, 2H), 3.48-3.56 (m, 8H), 3.71 (br s, 2H), 4.91 (br S, 2H), 7.25-7.27 (d, J=8.1 Hz, 2H), 7.30-7.36 (m, 5H), 7.57-7.59 (d, J=8.1 Hz, 2H); LRMS (ESI/APCI) m/z 411 [M]+

Workup

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

Sources & evidence

ORD record
ord-985a7375fa3942218b3918f28ac9cf41
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

Loading…