Triacetoxyperiodinane → HCID 86659685, compound

HRID 2400938Notes

Reaction equation

HRID 2400938 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([N:15]2[C:19](=[O:20])[C:18](=[CH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[C:39]([F:42])([F:41])[F:40])[N:26]=[CH:25]4)[S:17][C:16]2=[O:43])[CH2:9]1)=O)(C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:27]2[C:28]3[C:24](=[CH:23][C:22](/[CH:21]=[C:18]4/[C:19](=[O:20])[N:15]([CH:10]5[C:11](=[O:14])[CH2:12][CH2:13][NH:8][CH2:9]5)[C:16](=[O:43])[S:17]/4)=[CH:30][CH:29]=3)[CH:25]=[N:26]2)=[C:33]([C:39]([F:41])([F:42])[F:40])[CH:34]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86659686HCID 86659686, compound

Product 1

HCID 86659685HCID 86659685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{5-[1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazol-5-ylmethylene]-2,4-dioxothiazolidin-3-yl}-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (0.2 mmol) in DCM (2 mL) was added Dess-Martin periodinane powder (0.25 mmol). The mixture was stirred at rt for 18 h, then purified by silica gel chromatography (0-30% EtOAc/hexanes). The product was obtained as pale yellow solid, which was treated with TFA/DCM following General Procedure M to afford the title compound.

Workup

  1. custompurified by silica gel chromatography (0-30% EtOAc/hexanes)
  2. customThe product was obtained as pale yellow solid, which

Sources & evidence

ORD record
ord-bcc4bbe105694d22a37f4c99c56dde7a
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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