Triacetoxyperiodinane → HCID 131720906, compound

HRID 355325Notes

Reaction equation

HRID 355325 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[NH2:23][C@H:24]([C:32]([NH:34][CH2:35][C:36]([NH:38][C@H:39]([C:41]([OH:43])=O)[CH3:40])=[O:37])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[NH2:44][C@H:45]([CH2:50][OH:51])[CH2:46][CH:47]([CH3:49])[CH3:48].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:23][C@H:24]([C:32]([NH:34][CH2:35][C:36]([NH:38][C@H:39]([C:41]([NH:44][C@H:45]([CH:50]=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH3:40])=[O:37])=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 131720907HCID 131720907, compound

Product 1

HCID 131720906HCID 131720906, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

29.9 g (70.7 mol) of Dess-Martin periodinane was suspended in 500 ml CH2Cl2 and stirred for 10 min. Moc-Phe-Gly-Ala-Leucinol (10.6 g, 23.5 mol) was dissolved in 100 ml CH2Cl2 and added at a moderate rate to the periodinane slurry. The mixture was stirred for 1h and poured into 150 ml NaHCO3 containing 123 g Na2S2 O3. The mixture was allowed to stir for 15 min and extracted with EtOAc. The organic phase was dried and filtered followed by removal of solvent. Chromatography (3.5% MeOH/CH2Cl2) on silica gave 5.1 g of pure white solid that is a mixture of the methoxy hemiacetal and aldehyde. 13C NMR (CDCl3,CD3OD) 17.62, 17.94, 21.53, 21.71, 22.99, 23.30, 23.39, 24.54, 37.05, 37.70, 37.92, 38.24, 42.87, 49.83, 51.79, 52.14, 52.40, 56.75, 57.19, 98.40, 99.18, 127.00, 128.60, 129.06, 136.44, 157.27, 169.19, 169.67, 172.73, 173.40, 200.43.

Workup

  1. additionadded at a moderate rate to the periodinane slurry
  2. stirringto stir for 15 min
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customfollowed by removal of solvent

Sources & evidence

ORD record
ord-cf03e32e8cba425e86dc76fcc8dfcb0a
Source dataset
uspto-grants-1998_11
Patent number
US05830840

Reaction notes

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