Triacetoxyperiodinane → HCID 118025814, compound

HRID 1750552Notes

Reaction equation

HRID 1750552 reaction equation
[OH:1][CH:2]1[CH2:6][CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:4]([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]2[N:27]=[CH:26][CH:25]=[N:24]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[CH3:11])[CH:4]([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]2[N:27]=[CH:26][CH:25]=[N:24]2)[CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118025588HCID 118025588, compound

Product 1

HCID 118025814HCID 118025814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-{4-hydroxy-2-[2-(2H-1,2,3-triazol-2-yl)benzamido]cyclopentyl}carbamate (910 mg, 2.35 mmol) in dry DCM (12 ml) at 0° C. under an atmosphere of nitrogen was added Dess-Martin periodinane (3.4 g, 7.99 mmol). The reaction was warmed to room temperature for 2 hours then concentrated in vacuo. The crude material was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude material was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-d1c4635228cd4cfe896ebb9a2bf48812
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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