Triacetoxyperiodinane → HCID 178519990, compound

HRID 574675Notes

Reaction equation

HRID 574675 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:23])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][N:5]=[C:4]([CH2:24][OH:25])[N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:24]([C:4]1[N:3]=[C:2]([OH:1])[C:7]([NH:8][C:9](=[O:23])[CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][N:5]=1)=[O:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178522403HCID 178522403, compound

Product 1

HCID 178519990HCID 178519990, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound step E product, 3-g, (1.1 g, 3.2 mmol) in DCM was added slowly Dess-Martin reagent (1.6 g, 3.84 mmol) and stirred at room temperature for 20 min. The reaction mixture was concentrated and purified by column chromatography to afford the product, 3-h (1.0 g, 90%). LC-MS (M+H+H2O)+ 352.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-15b9e965036f43469c864b639cf003aa
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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