Ethanol → HCID 58812098, compound

HRID 2240003Notes

Reaction equation

HRID 2240003 reaction equation
[CH2:1]([OH:3])C.[C:4]1([S:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:36]=[CH:37][C:38]=2[N+:39]([O-])=O)[O:21][CH:22]([CH3:35])COS(C2C=CC(C)=CC=2)(=O)=O)(=[O:16])=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[CH2:42]1[CH2:46]O[CH2:44][CH2:43]1>[Pd]>[NH2:39][C:38]1[CH:37]=[CH:36][C:20]([O:21][CH2:22][CH2:35][CH2:1][O:3][S:14]([C:42]2[CH:46]=[CH:5][C:4]([CH3:13])=[CH:44][CH:43]=2)(=[O:16])=[O:15])=[CH:19][C:18]=1[CH2:17][S:14]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 87538692HCID 87538692, compound

Product 1

HCID 58812098HCID 58812098, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethanol (30 mL) and 10% palladium on carbon (0.439 g) were added to a hot solution of toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-propyl ester (0.785 g, 1.41 mmol) in hot, anhydrous THF (40 mL). The reaction mixture was hydrogenated on the Parr apparatus for 2 hours (starting pressure of 43 psi). The reaction mixture was then filtered over Celite and concentrated. It was dried at 75° C. in vacuo for 20 minutes to yield toluene-4-sulfonic acid 3-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-propyl ester as a brown-green semi-solid (0.627 g, 84.4%). Mass Spectrum (+EI, [M+H]+) m/z 526.

Workup

  1. filtrationThe reaction mixture was then filtered over Celite
  2. concentrationconcentrated
  3. customIt was dried at 75° C. in vacuo for 20 minutes

Sources & evidence

ORD record
ord-76bf1524ae5a4137a1cc761bf1f4f4b3
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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