HCID 11340609, compound → HCID 59814827, compound

HRID 2116666Notes

Reaction equation

HRID 2116666 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18][C:19]4[S:20][C:21]([C@:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][CH3:26])=[CH:22][N:23]=4)=[CH:15][CH:16]=3)[O:11][C:10](=[O:32])[CH:9]=2)=[CH:4][CH:3]=1.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:43].[Mg+2]>C(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([C:19]4[S:20][C:21]([C@:24]([OH:31])([C:27]([F:29])([F:30])[F:28])[CH2:25][CH3:26])=[CH:22][N:23]=4)=[O:43])=[CH:15][CH:16]=3)[O:11][C:10](=[O:32])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11340609HCID 11340609, compoundHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 59814827HCID 59814827, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-fluorophenyl)-7-({5-[(1R)-1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one (0.100 g, 0.2 mmol) in 7 ml of CH2Cl2 and 0.7 ml of MeOH, was added magnesium monoperoxyphthalate hexahydrate (0.051 g, 0.1 mmol). The mixture was stirred at rt overnight and partitioned between water and CH2Cl2. The layers were separated and the organic phase washed with brine, dried over MgSO4 and evaporated to dryness. The residue was chromatographed on silica gel (hexane/EtOAc; 8:2) to give two diastereoisomers. 1H NMR (400 MHz, CDCl3): δ 7.9 (s, 1H), 7.85 (s, 1H), 7.67 (dd, 2H), 7.45 (m, 2H), 7.25 (m, 2H), 6.47 (s, 1H), 2.12 (m, 2H), 0.92 (t, 3H). Diastereoisomer #2: 1H NMR (400 MHz, CDCl3): δ 7.9 (s, 1H), 7.82 (s, 1H), 7.67 (dd, 2H), 7.45 (m, 2H), 7.25 (m, 2H), 6.47 (s, 1H), 2.15 (m, 2H), 0.95 (t, 3H).

Workup

  1. custompartitioned between water and CH2Cl2
  2. customThe layers were separated
  3. washthe organic phase washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel (hexane/EtOAc; 8:2)
  7. customto give two diastereoisomers

Sources & evidence

ORD record
ord-487ebbaa3819461a9e8b58168de9d6b7
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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