Water → HCID 89870943, compound

HRID 516176Notes

Reaction equation

HRID 516176 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:31]1[C:32]2[C:39]([I:40])=[CH:38][N:37]([C@@H:41]3[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:43]([CH2:53][OH:54])[CH2:42]3)[C:33]=2[N:34]=[CH:35][N:36]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24].O>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:31]1[C:32]2[C:39]([I:40])=[CH:38][N:37]([C@@H:41]3[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[C@H:43]([CH:53]=[O:54])[CH2:42]3)[C:33]=2[N:34]=[CH:35][N:36]=1)=[O:29])([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 159087Triacetoxyperiodinane3×HCID 89871088HCID 89871088, compound

Product 1

HCID 89870943HCID 89870943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (51 mg) was added to a solution of (2S,4S)-tert-butyl 4-(4-(bis(tert-butoxycarbonyl)amino)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (66 mg) obtained in Step 4 in methylene chloride (2 ml), and the resulting mixture was stirred at room temperature for 1 hour. Dess-Martin periodinane (100 mg) was further added to the mixture, and stirred at room temperature for 1 hour. Dess-Martin periodinane (70 mg) was additionally added thereto, and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture to separate the organic layer. The organic layer was washed with a sodium hydrogen carbonate aqueous solution and a 10% sodium thiosulfate aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-yellow, amorphous substance (68 mg). Physical properties: m/z [M+H]+ 658.1

Workup

  1. stirringstirred at room temperature for 1 hour
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. customto separate the organic layer
  4. washThe organic layer was washed with a sodium hydrogen carbonate aqueous solution
  5. dry with materiala 10% sodium thiosulfate aqueous solution, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8f1f0d778168457dbe721cc1d06be205
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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