Tetrahydrofuran → HCID 68863511, compound

HRID 1725932Notes

Reaction equation

HRID 1725932 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]([OH:20])=[O:19])=[C:16](C)[C:15](C=C)=C[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:28]CC1.C([O-])(O)=O.[Na+].[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>O.O=[Os](=O)(=O)=O>[OH:28][CH:37]([C:38]1[C:16]([CH3:15])=[C:17]([C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[CH:13][CH:39]=1)[C:18]([OH:20])=[O:19])[CH2:41][OH:40]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 236477625,6-Disubstituted anthranilic acid sulfonamide, 9b

Product 1

HCID 68863511HCID 68863511, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

A solution of Example 173C (0.21 g, 0.62 mmol) in THF (8 mL) and water (1 mL) was treated with N-methylmorpholine oxide (0.11 g, 0.95 mmol) in one portion and dropwise with OsO4 (2.5% wt solution in tert-butanol, 0.5 mL). The mixture was stirred at room temperature for 4 hours, treated with water (20 mL), followed by 5% aqueous NaHCO3 (10 mL), and extracted with diethyl ether (2×10 mL). The aqueous solution was adjusted to pH 2.0 with 1N HCl and extracted with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) filtered, and concentrated to provide the desired product (101 mg, 43.5%). 1H NMR (DMSO-d6) δ 2.22 (s, 3H), 4.73 (m, 2H), 5.18 (m, 1H), 6.79 (d, 1H), 7.34 (d, 1H), 7.40 (m, 2H), 7.80 (m, 2H), 9.80 (br s, 1H), 12.90 (br s, 1H); MS (ESI(−)) m/e 368 (M−H)−.

Workup

  1. extractionextracted with diethyl ether (2×10 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c949eb55ec9c44ff8f88b8b61c1764a3
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…