5-Chlorothiophene-2-sulfonyl isoleucinol → 5-Chloro-N-[(S,S)-1-formyl-2-methylbutyl]thiophene-2-sulfonamide

HRID 398270Notes

Reaction equation

HRID 398270 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:21][C@H:22]([CH2:27][OH:28])[C@H:23]([CH2:25][CH3:26])[CH3:24])(=[O:20])=[O:19])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:21][C@H:22]([CH:27]=[O:28])[C@@H:23]([CH3:24])[CH2:25][CH3:26])(=[O:20])=[O:19])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 98793025-Chlorothiophene-2-sulfonyl isoleucinolHCID 178418287HCID 178418287, compound

Product 1

HCID 590862015-Chloro-N-[(S,S)-1-formyl-2-methylbutyl]thiophene-2-sulfonamideYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Molecular sieves (15 g, 4 Å) were stirred in dry CH2Cl2 (175 mL) for 10 min. Then a mixture of pyridinium chlorochromate (8.6 g, 39.9 mmol) and silica gel (9 g) was added and the mixture was stirred an additional 10 min. To the suspension was added 5-chlorothiophene-2-sulfonyl isoleucinol (4 g, 13.4 mmol) dissolved in CH2Cl2 (15 mL) and the resulting slurry was stirred for 2 h. The reaction mixture was filtered and the solvent was removed. The residue was subjected to a Biotage™ eluting with 20% EtOAc/hexane to give 3.22 g (81%) of the aldehyde (LCMS=294.21 (M−H), rt=1.10 min).

Workup

  1. additionwas added
  2. stirringthe resulting slurry was stirred for 2 h
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was removed
  5. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-bc3948bc8269481286914b7f901385b5
Source dataset
uspto-grants-2003_08
Patent number
US06610734B2

Reaction notes

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