4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester → 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

HRID 22876Notes

Reaction equation

HRID 22876 reaction equation
[C:1]([O:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)(=[O:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[Ni]>[C:1]([O:5][C:6](=[O:27])[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])(=[O:17])=[O:16])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 697944154-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 207553664-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester (14.4 g, 40 mmol) was dissolved in 100 mL of tetrahydrofuran containing 10 g of Raney Nickel. The reaction was pressurized with 100 psi of hydrogen gas and stirred for 28 hours at 25° C. to 60° C. The reaction was filtered, and the filtrate was rotary evaporated to give a thick oil. Chromatography (20% ethyl acetate/hexanes, SiO2) of the oil gave 12.2 (92%) of 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester as a clear oil. 1H-NMR (CDCl3); δ 7.85 (d, 2H), 7.70 (dd, 1H), 7.27 (m, 3H), 6.78 (m, 2H), 5.18 (bt, 1H), 4.82 (bs, 2H), 4.08 (d, 2H), and 1.57 (s, 9H). MS: M+=363.1 Da Step (3): Synthesis of 4-[(2-Amino-5-bromo-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate was rotary evaporated
  3. customto give a thick oil

Sources & evidence

ORD record
ord-b68334b895c84ed6b3ec79141c1b7f82
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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