Di-tert-butyl (((((1,3-phenylenebis(methylene))bis(azanediyl))bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate → N1,N1'-(1,3-Phenylenebis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine)
Reaction equation
[C:1]1([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH:33]C(=O)OC(C)(C)C)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:2]=1>Cl>[C:1]1([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:2]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To the crude di-tert-butyl (((((1,3-phenylenebis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate from Step 1 was added methanolic HCl (150 mL, 1.0 M). The reaction mixture was stirred for 2 h and concentrated under reduced pressure. The solid was collected by vacuum filtration, and it was washed with Et2O (30 mL) and hot MeOH (30 mL) to afford the desired product (1.1 g, 56%) as a white solid. 1H NMR (500 MHz, D2O) δ ppm 7.62 (s, 4H), 4.36 (s, 4H), 3.28-3.21 (m, 12H), 3.15 (t, J=8.0 Hz, 4H), 2.23-2.11 (m, 8H). 13C NMR (125 MHz, D2O) 131.4, 131.3, 131.1, 130.2, 50.8, 44.7, 44.6, 44.1, 36.5, 23.6, 22.6. LRMS [M+H]+365.3.
Workup
- concentrationconcentrated under reduced pressure
- filtrationThe solid was collected by vacuum filtration, and it
- washwas washed with Et2O (30 mL) and hot MeOH (30 mL)
Sources & evidence
- ORD record
- ord-72e24c58405144a1a6240b93763de8a6
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439433B2
Reaction notes
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