HCID 87954650, compound → HCID 86588196, compound

HRID 1814274Notes

Reaction equation

HRID 1814274 reaction equation
[C:1]([O:5][C:6](=[O:41])[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][CH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[Ni]>[C:1]([O:5][C:6](=[O:41])[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][CH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 87954650HCID 87954650, compound

Product 1

HCID 86588196HCID 86588196, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methoxy-N-methyl-3-[2-(2-naphthalen-1-yl-ethoxy)-4-nitro-benzenesulfonylamino]-succinamic acid tert-butyl ester (0.52 g) in tetrahydrofuran (35 mL) and ethanol (35 mL) was treated with RaNi (0.3 g) and hydrogenated at 50 psi. The solution was filtered through Celite and evaporated to give the desired aniline derivative 3-[4-amino-2-(2-naphthalen-1-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.45 g) as an amorphous foam.

Workup

  1. filtrationThe solution was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-f9e3920b52c34716b1876c005cb00b38
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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