Diethyl Ether → (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid

HRID 627083Notes

Reaction equation

HRID 627083 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][OH:32])[CH:20]=[C:19]1[CH3:33])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].CC[O:36]CC>C(#N)C.I(O)(=O)(=O)=O.[O-2].[Cr+3].[O-2].[O-2].[Cr+3]>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C@H:21]([C:31]([OH:36])=[O:32])[CH:20]=[C:19]1[CH3:33])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 89851797(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89851803(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 131735278Periodic acid chromium oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 18, 5 g, 10.34 mmol) in wet acetonitrile (60 mL) (0.75% by volume) at 0° C. was added dropwise the previously formed periodic acid/chromium oxide solution (60 mL, 3 eq). After 30 minutes the reaction was complete by LC/MS. The reaction mixture was diluted with ether and washed with 10% citric acid, saturated sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated to afford an orange foam (4.16 g, 81%).

Workup

  1. washwashed with 10% citric acid, saturated sodium bicarbonate and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-efd630b59ede4f44b194a0c5be0bd882
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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