3-(2-benzyloxy-4-nitro-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester → 3-(4-amino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:20]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CO.[Ni]>[C:1]([O:5][C:6](=[O:36])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The 3-(2-benzyloxy-4-nitro-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester was dissolved in 1:1 THF/MeOH, and Raney Ni added. The solution was hydrogenated at 30 psi. When the reaction was complete, the solvent was removed to give the crude give 3-(4-amino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester. The product can be used crude, or chromatographed with 7.5% methanol/ethyl acetate. 1H NMR (CDCl3) 7.65-7.3 (8H, m), 6.2 (2H, m), 5.78 (2H, d, J=9.76 Hz), 5.2-5.1 (2H, m), 4.8-4.7 (1H, m), 4.2-4.0 (2H, br), 3.59 (3H, s), 2.56 (3H, s), 2.6-2.4 (2H, m), 1.41 (9H, s). MS (m/z) (M+1)=494.
Workup
- additionadded
- customthe solvent was removed
- customto give the crude
Sources & evidence
- ORD record
- ord-c9fd686453ac47e89cd725539f67bda6
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875765B2
Reaction notes
Loading…