Triacetoxyperiodinane → tert-butyl (1R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-oxocyclohexylcarbamate

HRID 705284Notes

Reaction equation

HRID 705284 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]([C:15]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[C@H:24]2[CH2:29][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C@H:27]([OH:38])[C@@H:26]([CH3:39])[CH2:25]2)=[O:16])[CH:12]=[CH:11][C:10]=1[F:40].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]([C:15]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[C@H:24]2[CH2:29][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:36])[CH3:34])[C:27](=[O:38])[C@@H:26]([CH3:39])[CH2:25]2)=[O:16])[CH:12]=[CH:11][C:10]=1[F:40]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86639738tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

Product 1

HCID 86705245tert-butyl (1R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-oxocyclohexylcarbamateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate (1.0 equiv.) in DCM (0.10 M) was added Dess-MartinPeriodinane (1.2 equiv.). The flask was capped and the homogeneous solution was left stirring at rt for 3 hrs. The solution was partitioned between EtOAc and 1:1 10% Na2S2O3/NaHCO3 (sat.). The organic layer was washed with NaCl(sat.), dried over MgSO4, filtered and concentrated, and purified by ISCO SiO2 chromatography to yield tert-butyl (1R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-oxocyclohexylcarbamate in 83% yield. LC/MS (m/z)=555.4 (MH+), Rt=0.87 min.

Workup

  1. customThe flask was capped
  2. waitthe homogeneous solution was left
  3. customThe solution was partitioned between EtOAc and 1:1 10% Na2S2O3/NaHCO3 (sat.)
  4. washThe organic layer was washed with NaCl(sat.)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by ISCO SiO2 chromatography

Sources & evidence

ORD record
ord-fb0879a8b7c94406a0f3c66a66d5fcbc
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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