HCID 21078694, compound → HCID 10335343, compound

HRID 1375190Notes

Reaction equation

HRID 1375190 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:11]([NH:14][C@H:15]([CH2:20][OH:21])[C@@H:16]([CH3:19])[CH2:17][CH3:18])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([S:11]([NH:14][C@H:15]([CH2:20][OH:21])[C@@H:16]([CH3:19])[CH2:17][CH3:18])(=[O:12])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 2

HCID 21078694HCID 21078694, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10335343HCID 10335343, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A standard hydrogenation bottle was charged with 3-nitro-4-chloro-N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]benzenesulfonamide (0.50 g, 1.48 mmol), 10% palladium on carbon (0.05 g), methanol (25 mL) and hydrogen gas. It was shaken on a Parr hydrogenation apparatus for 50 minutes. The reaction mixture was filtered and the solvent evaporated to produce a crude oil that was flash chromatographed (eluant: ethyl acetate-hexane, 3–2) to afford the product as a solid, mp 89–92° C. (0.12 g, 26%). MS (+APCI) 307.03 ([M+H]+). Anal. Calc'd for C12H19ClN2O3S: C, 46.98; H, 6.24; N, 9.13; Found: C, 47.44; H, 6.32; N, 8.88.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated
  3. customto produce a crude oil that
  4. customchromatographed (eluant: ethyl acetate-hexane, 3–2)

Sources & evidence

ORD record
ord-02757a85862c4227aa9f53b2eff3996d
Source dataset
uspto-grants-2007_01
Patent number
US07166622B2

Reaction notes

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