Triacetoxyperiodinane → HCID 178493278, compound

HRID 630404Notes

Reaction equation

HRID 630404 reaction equation
[OH:1][C:2]([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][O:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH2:28][OH:29])=[CH:22][C:21]=2[Cl:30])=[O:18])[CH3:13])[CH2:8][CH2:7]1)=[O:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[OH:1][C:2]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][O:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH:28]=[O:29])=[CH:22][C:21]=2[Cl:30])=[O:18])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178493279HCID 178493279, compound2×

Product 1

HCID 178493278HCID 178493278, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

trans-4-[{2-[({[2-chloro-4-(hydroxymethyl)-5-methoxyphenyl]amino}carbonyl)oxy]ethyl}-(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 62; 200 mg; 0.33 mmol) was dissolved in 8 ml dichloromethane and stirred at room temperature in an inert atmosphere. Dess-Martin reagent (170 mg; 0.40 mmol) was added in 3 portions and the reaction stirred for 30 min. Dichloromethane (15 ml) was added, the solution was washed with 4% aqueous sodium hydrogen carbonate solution and vigorously stirred for 1 hour. The solid was filtered and the organic phase of the filtrate was washed with brine, dried and concentrated to give 197 mg of the title compound enough pure to continue with the next step.

Workup

  1. stirringthe reaction stirred for 30 min
  2. washthe solution was washed with 4% aqueous sodium hydrogen carbonate solution
  3. stirringvigorously stirred for 1 hour
  4. filtrationThe solid was filtered
  5. washthe organic phase of the filtrate was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-883187124a944d1ea10e6e93e38652c7
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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