Triacetoxyperiodinane → HCID 86638994, compound

HRID 656227Notes

Reaction equation

HRID 656227 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@@H:12]([S:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([OH:24])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>ClCCl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([S:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11](=[O:24])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21584019Toluene ethylacetateHCID 54673740HCID 54673740, compound

Product 1

HCID 86638994HCID 86638994, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of thiobenzoic acid S-((1R,2R,4R)-4-tert-butoxycarbonylamino-2-hydroxy-cyclohexyl) ester+(1S,2S,4S) diastereomer (5 g, 14.2 mmol), 4 Å-molecular sieve (3 g) 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one (6.33 g, 15 mmol) in 100 ml of dichloromethane was stirred under argon at 5° C. for 1 hour and 1 hour at room temperature. The mixture was filtered over celite, dried and concentrated under vacuum to give the crude product. After chromatography of the mixture (silica, toluene/ethyl acetate=7/1) the title compound (toluene/ethyl acetate=3/1, Rf=0.48, 4.18 g, 84% yield) was obtained as a white solid.

Workup

  1. filtrationThe mixture was filtered over celite
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customto give the crude product

Sources & evidence

ORD record
ord-9bcbf87cf7dd4eaf91ea07006ae929f3
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

Loading…