Triacetoxyperiodinane → HCID 58530831, compound

HRID 2400936Notes

Reaction equation

HRID 2400936 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18](=[O:19])/[C:17](=[CH:20]/[C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[C:38]([F:41])([F:40])[F:39])[N:25]=[CH:24]4)/[S:16][C:15]2=[O:42])[CH:10]([OH: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:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:26]2[C:27]3[C:23](=[CH:22][C:21](/[CH:20]=[C:17]4/[C:18](=[O:19])[N:14]([CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][C:10]5=[O:43])[C:15](=[O:42])[S:16]/4)=[CH:29][CH:28]=3)[CH:24]=[N:25]2)=[C:32]([C:38]([F:41])([F:40])[F:39])[CH:33]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86659683HCID 86659683, compound

Product 1

HCID 58530831HCID 58530831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5Z)-4-{5-[1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazol-5-ylmethylene]-2,4-dioxothiazolidin-3-yl}-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (0.13 mmol) in DCM (2 mL) was added Dess-Martin periodinane powder (0.16 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-5e6df9a1cdd24cc4b0343cd164230d0a
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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