Cornforth reagent → HCID 10193197, compound

HRID 1176143Notes

Reaction equation

HRID 1176143 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[S:27][C:26]([S:28]([NH:31][C@H:32]([CH2:38][OH:39])[CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])(=[O:30])=[O:29])=[CH:25][CH:24]=1>C(Cl)Cl>[Cl:22][C:23]1[S:27][C:26]([S:28]([NH:31][C@H:32]([CH:38]=[O:39])[CH:33]([CH2:34][CH3:35])[CH2:36][CH3:37])(=[O:30])=[O:29])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 11358855GSI-136

Product 1

HCID 10193197HCID 10193197, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium dichromate (2.4 g, 6.4 mmol) was added to a solution of 5-chloro-N-[(S)-2-ethyl-1-(hydroxymethyl)butyl]-2-thiophenesulfonamide (0.5 g, 1.6 mmol) in CH2Cl2 (20 mL). After 18 h, the reaction mixture was filtered through a plug of Celite. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (eluant: 1:4 EtOAc-hexane) to give 5-chloro-N-[(S)-2-ethyl-1-formylbutyl]thiophene-2-sulfonamide as a white solid (303 mg, 61%). [a]D25=+136.76° (c=1% SOLUTION, CHCl3). Mass Spectrum (−ESI): 308 (M−H)−. Anal. Calc'd for C11H16ClNO3S2: C, 42.64; H, 5.21; N, 4.52. Found: C, 42.57; H, 5.24; N, 4.52.

Workup

  1. filtrationthe reaction mixture was filtered through a plug of Celite
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (eluant: 1:4 EtOAc-hexane)

Sources & evidence

ORD record
ord-b761fe60a8df4d869b73a3cff946598a
Source dataset
uspto-grants-2010_11
Patent number
US07842718B2

Reaction notes

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