Triacetoxyperiodinane → HCID 59843139, compound

HRID 2196566Notes

Reaction equation

HRID 2196566 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])=[O:16])=[CH:13][C:12]([C:27]([F:30])([F:29])[F:28])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:2]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])=[O:16])=[CH:13][C:12]([C:27]([F:30])([F:28])[F:29])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59843268HCID 59843268, compound

Product 1

HCID 59843139HCID 59843139, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 153 (650 mg, 1.550 mmol) in DCM (7.75 ml) under N2 was added Dess-Martin periodinane (0.50 ml, 1.627 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was taken to dryness and the residue was purified by chromatography (Biotage 15 to 65% EtOAc in hexane) to afford 154 (565 mg, 1.35 mmol, 88%). LRMS (ESI): (calc.) 417.1 (found) 440.2 (MNa)+.

Workup

  1. customthe residue was purified by chromatography (Biotage 15 to 65% EtOAc in hexane)

Sources & evidence

ORD record
ord-53c44f5e275a4bafb3a293ceda7f1790
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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