Thiophene → 2-(2-Amino-5-benzoyl-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

HRID 2088836Notes

Reaction equation

HRID 2088836 reaction equation
[CH:1]1([N:7]([CH3:32])[S:8]([CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH:17][C:16]=2[N+:29]([O-])=O)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S1C=CC=C1>CO.[Pd]>[CH:1]1([N:7]([CH3:32])[S:8]([CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH:17][C:16]=2[NH2:29])(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 586251122-(5-Benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

Product 1

HCID 586251322-(2-Amino-5-benzoyl-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(5-benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide (0.009 mol) in methanol (150 mL) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of thiophene solution (1 mL). After uptake of H2 (3 equiv.), the catalyst was filtered off, and the filtrate was evaporated. The residue was purified by column chromatography over Biotage (eluent: 98:2 CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. filtrationAfter uptake of H2 (3 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over Biotage (eluent: 98:2 CH2Cl2:CH3OH)
  4. customThe purest product fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7e714d7b01324e28960efd98c535a2d1
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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