Triacetoxyperiodinane → (S)-N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide

HRID 57385Notes

Reaction equation

HRID 57385 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:48])[CH2:31][NH:32][C:33](=[O:47])[C@@H:34]([N:36]2[C:44](=[O:45])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]2=[O:46])[CH3:35])=[CH:26][CH:25]=1>ClCCl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:48])[CH2:31][NH:32][C:33](=[O:47])[C@@H:34]([N:36]2[C:44](=[O:45])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]2=[O:46])[CH3:35])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 90416129(2S)-N-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide

Product 1

HCID 90414725(S)-N-(2-(4-chlorophenyl)-2-oxoethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (3.091 g, 7.29 mmol) was added to a solution of (2S)—N-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide (2.173 g, 5.83 mmol) in dichloromethane (20 ml) and allowed to stir for 2 hours. Dilute w/dichloromethane (50 ml), wash w/a sol'n of sat. sodium bicarbonate and 10% Na2S2O3 solution, dry, concentrate in vacuo. 2.162 g (Used directly in the next step without further purification. HRMS(B) tR=1.24 min; MS m/z 371.2

Workup

  1. additionDilute
  2. washwash
  3. customdry
  4. concentrationconcentrate in vacuo
  5. custom2.162 g (Used directly in the next step without further purification

Sources & evidence

ORD record
ord-6828342fcdba45778caadae9a7b60df9
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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