HCID 10201990, compound → HCID 21114424, compound

HRID 1767582Notes

Reaction equation

HRID 1767582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16]([S:27][CH3:28])=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:29].[OH:30]OS([O-])=O.[K+]>C1COCC1.O.CCOC(C)=O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2=[N:15][C:16]([S:27]([CH3:28])=[O:30])=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:29]

Participants

6

Reactant 2

HCID 10201990HCID 10201990, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21114424HCID 21114424, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of example 2 (204 mg, 0.49 mmol) in THF was treated dropwise with oxone® (0.307 g, 0.5 mmol) in H2O (10 mL). The mixture was stirred at 23° for 2 h, diluted with EtOAc (100 mL) and washed with H2O (2×25 mL) and satd aq NaCl (25 mL), dried (Na2SO4), and concentrated. The residue was purified by prep hplc to afford the sulfoxide as a white powder. LC MS m/z=433 (MH+), Rt=1.70 min

Workup

  1. washwashed with H2O (2×25 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by prep hplc

Sources & evidence

ORD record
ord-f6c4fa60d722432aa591beff10518d8f
Source dataset
uspto-grants-2007_06
Patent number
US07235551B2

Reaction notes

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