HCID 58981098, compound → HCID 58980924, compound

HRID 1181847Notes

Reaction equation

HRID 1181847 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([CH2:15][OH:16])[N:12]([CH3:14])[CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O=[Mn]=O>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([CH:15]=[O:16])[N:12]([CH3:14])[CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58981098HCID 58981098, compound

Product 1

HCID 58980924HCID 58980924, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4 (6.40 g, 25.98 mmol) in dry THF (750 mL) under nitrogen was charged with MnO2 (65.0 g, 0.64 mol) and was allowed to stir at room temperature for 1 h. The mixture was filtered through celite; the filtrate was concentrated. Purification by flash chromatography on silica gel using 10-25% EtOAc/hexanes gradient as eluent afforded 1 (5.67 g, 89%) as a white solid. Mp 97-98° C. 1H NMR (300 MHz, CDCl3): δ 9.95(d, 0.8 Hz, 1H), 7.33 (bs, 1H), 7.18 (d, 1.9 Hz, 1H), 4.69 (bs, 1H), 3.97 (s, 3H), 1.27 (s, 9H). MS m/z: 243 (M−1). Analysis calcd. for C10H16N2O3S; C, 49.16; H, 6.60, N, 11.47; found, C, 48.99; H, 6.70; N, 11.45.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography on silica gel using 10-25% EtOAc/hexanes gradient as eluent

Sources & evidence

ORD record
ord-7969a28df84e4af9807442f8e8a2563e
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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