Triacetoxyperiodinane → HCID 21049003, compound

HRID 2212392Notes

Reaction equation

HRID 2212392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][C@@H:23]([OH:26])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:12][CH2:13][CH:14]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]3)(=[O:20])=[O:19])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58697159HCID 58697159, compound

Product 1

HCID 21049003HCID 21049003, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 181 (89 mg, 0.17 mmol) in dichloromethane (5 ml) was treated with Dess Martin periodinane (212 mg, 0.5 mmol) and stirred at room temperature for 2 hours. The resulting mixture was filtered through celite and evaporated to an oil which was purified by chromatography (50% ethyl acetate/hexane) to yield a white solid (69 mg). 1H NMR (360 MHz, CDCl3) δ 7.39–7.29 (4H, m), 7.08–7.04 (2H, m) 6.88–6.82 (1H, m), 5.00 (1H, d, J=6.8 Hz), 3.70–3.60 (5H, m), 2.65–2.56 (4H, m), 2.46–2.38 (2H, m), 2.04–2.00 (2H, m), 1.58–1.50 (2H, m). m/z=533, 535[MH]+

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. customevaporated to an oil which
  3. customwas purified by chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e8d85c90918542c69c9383d55f358284
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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