Triacetoxyperiodinane → HCID 58485787, compound

HRID 1396177Notes

Reaction equation

HRID 1396177 reaction equation
[C:1]([O:5][C:6](=[O:46])[N:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[C:32]3[C:31]([CH:33]4[CH2:35][CH2:34]4)=[N:30][CH:29]=[N:28][C:27]=3[N:26]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:25]=2)[OH:23])=[C:18]([F:45])[N:17]=1)[C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6](=[O:46])[N:7]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[C:32]3[C:31]([CH:33]4[CH2:34][CH2:35]4)=[N:30][CH:29]=[N:28][C:27]=3[N:26]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:37])=[O:38])[CH:25]=2)=[O:23])=[C:18]([F:45])[N:17]=1)[C:8]1[CH:9]=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58485824HCID 58485824, compound

Product 1

HCID 58485787HCID 58485787, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{5-[(7-Benzenesulfonyl-4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(6-methoxy-pyridin-3-yl)-carbamic acid tert-butyl ester (75, 0.350 g, 0.541 mmol) is alternatively dissolved in 10.0 mL of dichloromethane, and Dess-Martin periodinane (0.211 g, 0.498 mmol) is added. The reaction is stirred at room temperature for 30 minutes, then concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 10-100% ethyl acetate in hexane. Appropriate fraction are combined and concentrated under vacuum to provide the desired compound (77, 340 mg). MS (ESI) [M+H+]+=645.4.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resulting material is purified by silica gel column chromatography
  3. washeluting with 10-100% ethyl acetate in hexane
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-78bafd8ac4b140b1b55b1ff4bdce0164
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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