HCID 58812135, compound → HCID 58812092, compound

HRID 2239988Notes

Reaction equation

HRID 2239988 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:12]=[C:13]([CH:28]=[CH:29][C:30]=2[N+:31]([O-])=O)[O:14][CH2:15][CH2:16][O:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.C(O)C.[Pd]>[NH2:31][C:30]1[CH:29]=[CH:28][C:13]([O:14][CH2:15][CH2:16][O:17][S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])=[CH:12][C:11]=1[CH2:10][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:8])=[O:9]

Participants

5

Reactant 1

HCID 58812135HCID 58812135, compound

Product 1

HCID 58812092HCID 58812092, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonylmethyl-4-nitro-phenoxy)-ethyl ester (13.1 g, 26.7 mmol) in THF (350 mL) and ethanol (250 mL) was added to 10% palladium on carbon (5.8 g) and hydrogenated on the Parr apparatus with for one hour (starting pressure of 30-40 psi.). The mixture was filtered over Celite, concentrated and dried in vacuo at 80° C. for 30 minutes to yield toluene-4-sulfonic acid 2-(4-amino-3-benzenesulfonylmethyl-phenoxy)-ethyl ester as a light yellow solid (11.7 g, 95.1%): MP: 144-6° C.; Mass spectrum (+EI, [M+H]+) m/z 462.

Workup

  1. customhydrogenated on the Parr apparatus with for one hour (starting pressure of 30-40 psi.)
  2. filtrationThe mixture was filtered over Celite
  3. concentrationconcentrated
  4. customdried in vacuo at 80° C. for 30 minutes

Sources & evidence

ORD record
ord-062a543d74ac4632abf61c5184d9ff89
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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