Triacetoxyperiodinane → Cbz-D-Phenylalaninal

HRID 340442Notes

Reaction equation

HRID 340442 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31](=[O:43])[NH:32][C@H:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:34][OH:35])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:23]([O:30][C:31](=[O:43])[NH:32][C@H:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:34]=[O:35])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 736170Benzyl hydrogen (1-hydroxy-3-phenylpropan-2-yl)carbonimidate

Product 1

HCID 10779332Cbz-D-PhenylalaninalYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (849 mg) was added to a dichloromethane (20 ml) solution containing benzyl((2R)-1-hydroxy-3-phenylpropan-2-yl)carbamate (571 mg), followed by stirring at room temperature for 3 hours and 30 minutes. Insoluble matter was removed by filtration, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1), and a white solid of benzyl((2R)-1-oxo-3-phenylpropan-2-yl)carbamate (501 mg) was thus obtained.

Workup

  1. customInsoluble matter was removed by filtration
  2. distillationthe solvent was distilled away under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1 to 2:1)

Sources & evidence

ORD record
ord-b8a012688812459fba1eeb23131bb807
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

Loading…