Triacetoxyperiodinane → N-[(1,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic Acid, T-Butyl Ester

HRID 634921Notes

Reaction equation

HRID 634921 reaction equation
[CH3:1]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C[C:24]1([C:34]([NH:36][C@H:37]([C:41]([NH:43][CH:44]([CH:53]([OH:65])[CH2:54][O:55][CH2:56][C:57]2[C:62]([Cl:63])=[CH:61][CH:60]=[CH:59][C:58]=2[Cl:64])[CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:42])[CH:38]([CH3:40])[CH3:39])=[O:35])[C:32]([CH3:33])=[C:31]2[C:26]([CH:27]=[CH:28][CH:29]=[CH:30]2)=[N:25]1>CS(C)=O>[CH3:1][N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]([CH3:33])=[C:24]1[C:34]([NH:36][C@H:37]([C:41]([NH:43][CH:44]([C:53](=[O:65])[CH2:54][O:55][CH2:56][C:57]1[C:62]([Cl:63])=[CH:61][CH:60]=[CH:59][C:58]=1[Cl:64])[CH2:45][C:46]([O:48][C:49]([CH3:50])([CH3:52])[CH3:51])=[O:47])=[O:42])[CH:38]([CH3:39])[CH3:40])=[O:35]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86756357N-[(2,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2',6'-dichlorobenzyloxy)pentanoic acid, t-butyl ester

Product 1

HCID 86584003N-[(1,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic Acid, T-Butyl EsterYield 86.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dess-Martin periodinane (195 mg) was added as a solid to a solution of N-[(2,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2′,6′-dichlorobenzyloxy)pentanoic acid, t-butyl ester (96 mg) in DMSO (1.5 ml). The resulting solution was stirred under a nitrogen atmosphere at room temperature for thirty minutes, hen partitioned between EtOAc and water. The organic phase was washed with water 2×) and brine, dried (Na2SO4), and concentrated to give a white solid (83 mg). Flash chromatographic purification with EtOAc/hexanes (1:1) afforded the title product as a white solid (54 mg). TLC (EtOAc/hexanes; 1:1, silica gel): Rf=0.52.

Workup

  1. customhen partitioned between EtOAc and water
  2. washThe organic phase was washed with water 2×) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ecd5689f1489422ab18fc7984bd370b3
Source dataset
uspto-grants-2001_02
Patent number
US06184244B2

Reaction notes

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