Triacetoxyperiodinane → HCID 86708931, compound

HRID 1522083Notes

Reaction equation

HRID 1522083 reaction equation
[OH:1][CH:2]1[CH2:7][N:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[S:5](=[O:18])(=[O:17])[N:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:18]=[S:5]1(=[O:17])[N:6]([C:8]2[C:9]([Cl:16])=[CH:10][C:11]([Cl:15])=[CH:12][C:13]=2[Cl:14])[CH2:7][C:2](=[O:1])[CH2:3][N:4]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86708932HCID 86708932, compound

Product 1

HCID 86708931HCID 86708931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 2-(4-hydroxy-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate (400 mg, 0.96 mmol) in dichloromethane (20 mL), was added Dess-Martin periodinane (1.30 g, 3.07 mmol) and agitated for 5 hr at room temperature. The resultant was washed with ethyl acetate (50 mL) and the white solid formed thus was filtered through celite upon washing with ethyl acetate (50 mL). The filtrate was concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=7:3), giving the compound of interest (344 mg, 86%, white solid). 1H NMR (300 MHz, DMSO-d6): δ 7.83 (s, 2H), 4.45 (s, 2H), 4.40 (s, 2H), 4.25 (s, 2H), 4.18-4.10 (q, 2H, J=7.1, 7.1, 7.1 Hz), 1.22-1.17 (t, 3H, J==7.1, 7.1 Hz).

Workup

  1. washThe resultant was washed with ethyl acetate (50 mL)
  2. customthe white solid formed thus
  3. filtrationwas filtered through celite
  4. washupon washing with ethyl acetate (50 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (hexane:ethyl acetate=7:3)
  7. customgiving the compound of interest (344 mg, 86%, white solid)

Sources & evidence

ORD record
ord-b181650fd83d4ba5af9a9b405b799b94
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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