Triacetoxyperiodinane → HCID 86638995, compound

HRID 656228Notes

Reaction equation

HRID 656228 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@@H:13]([S:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:12]([OH:24])[CH2:11][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>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH:13]([S:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12](=[O:24])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86638996HCID 86638996, compound

Product 1

HCID 86638995HCID 86638995, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

Thiobenzoic acid S-((1R,2R,5S)-5-tert-butoxycarbonylamino-2-hydroxy-cyclohexyl) ester+(1S,2S,5R) diastereomer (8.7 g, 24.8 mmol) from Example 34 Step A was treated with 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one (11.02 g, 26 mmol) according to the method of Example 34 Step B. After work up and chromatography (silica, toluene/ethyl acetate=6/1) of the mixture the title compound (toluene/ethyl acetate=3/1, Rf=0.43, 7.15 g, 83% yield) was obtained as a white solid.

Sources & evidence

ORD record
ord-500f8aeda0f84cb9ac6ef475d9a86252
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

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