Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate → 3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride
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.[Cl:20][CH2:21][CH2:22][CH:23](CC)[CH2:24][O:25][CH2:26][CH:27](CCCl)CC>>[Cl-:20].[CH2:1]([O:8][C:9]([NH:10][C:11]([CH3:12])([CH3:18])[CH2:13][CH2:14][N+:15]([CH2:27][CH2:26][O:25][CH2:24][CH2:23][CH2:22][CH3:21])([CH3:16])[CH3:17])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 75 °C
Procedure
A mixture of benzyl(4-(dimethylamino)-2-methylbutan-2-yl)carbamate (500 mg, 1.9 mmol, preparation described in previous experiment) and 2-(chloroethyl)-n-butyl ether (517 mg, 3.8 mmol) was stirred overnight at 75° C. An additional portion of 2-(chloroethyl)-n-butyl ether (517 mg, 3.8 mmol) was added and the mixture stirred for 24 hours at 80° C. The resultant white precipitate was collected on a glass fritted filter and washed with ether to give 388 mg of a white solid (51%). 1H NMR (400 MHz, MeOD) δ 0.86-0.89 (t, J=7.4 Hz, 3H), 1.23 (s, 6H), 1.27-1.33 (sext, J=7.5 Hz, 2H), 1.45-1.50 (m, 2H), 2.05-2.09 (m, 2H), 3.03 (s, 6H), 3.29-3.34 (m, 2H), 3.39-3.34 (t, J=Hz, 2H), 3.48-3.50 (br m, 2H), 3.74 (br s, 2H), 4.99 (s, 2H), 7.17 (s, 1H), 7.31-7.36 (m, 5H). LRMS (ESI/APCI) m/z 365 [M]+.
Workup
- stirringthe mixture stirred for 24 hours at 80° C
- customThe resultant white precipitate was collected on a glass fritted filter
- washwashed with ether
Sources & evidence
- ORD record
- ord-1e70bed4351d47878a8ac124bcc4f3a6
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248117B2
Reaction notes
Loading…