Triacetoxyperiodinane → HCID 24765490, compound

HRID 1255129Notes

Reaction equation

HRID 1255129 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH2:12][OH:13])[N:11]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[C:10]([CH:12]=[O:13])[N:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24765213HCID 24765213, compound

Product 1

HCID 24765490HCID 24765490, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution of Compound 39 (100 mg, 0.24 mmol) in 2 mL of CH2Cl2 was added Dess-Martin periodinane (127 mg, 0.3 mmol) at 0° C. The solution was stirred at 0° C. for 1 hour and warmed to room temperature. The reaction was concentrated. The residue was purified by column chromatography on silica gel (1-5% MeOH in CH2Cl2) to give Compound 67 (93 mg, 94%) as a white solid.

Workup

  1. temperaturewarmed to room temperature
  2. concentrationThe reaction was concentrated
  3. customThe residue was purified by column chromatography on silica gel (1-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-49934da985f040ecb9f3fe2239f9e1e7
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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