Triacetoxyperiodinane → HCID 178472414, compound

HRID 2202741Notes

Reaction equation

HRID 2202741 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:42])[C:7]=1[CH:8]([OH:41])[CH2:9][N:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:42][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8](=[O:41])[CH2:9][N:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178472403HCID 178472403, compound

Product 1

HCID 178472414HCID 178472414, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 1-2 (9.9 g, 15.6 mmol) in DCM (120 mL) was added Dess-Martin periodinane (21.9 g, 21.9 mmol) in portions, and the mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with NaHCO3 (50 mL, sat. aq.) and Na2S2O3 (50 mL, sat. aq.), then extracted with DCM (2×150 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: 10% EtOAc/hexane) to yield compound 1-3 (9.12 g, 92%) as a white solid. 1H NMR (CDCl3) rotomers present δ 8.74 and 8.67 (2H, 2×s); 7.85 and 7.79 (1H, 2×s); 7.30-7.26 (1H, m); 7.41-7.37 and 7.22-7.15 (3H, 2×m); 4.73-4.51 (4H, m); 4.27-4.21 (1H, m); 4.07 (2H, q, J=7.2 Hz); 2.50-2.48 (1H, m); 2.06-1.93 (6H, m); 1.59-1.54 (2H, m); 1.18 (3H, t, J=6.9 Hz); LCMS: 629 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with NaHCO3 (50 mL, sat. aq.) and Na2S2O3 (50 mL, sat. aq.)
  2. extractionextracted with DCM (2×150 mL)
  3. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, eluent: 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-a6abed01c9d845a4bc6dd8b36ef0d0bb
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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