Tetrahydrofuran → HCID 57526812, compound

HRID 1452638Notes

Reaction equation

HRID 1452638 reaction equation
O1CCCC1.[CH2:6]([C:9]1[C:10]([NH:35][C@H:36]2[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]2)=[N:11][C:12]2[N:13]([N:32]=[CH:33][CH:34]=2)[C:14]=1[N:15]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1)[CH:7]=C.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[C:28]([O:27][C:25]([N:15]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH3:24])=[CH:20][CH:21]=1)[C:14]1[N:13]2[C:12](=[CH:34][CH:33]=[N:32]2)[N:11]=[C:10]2[C:9]=1[CH:6]=[CH:7][N:35]2[C@H:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]1)=[O:26])([CH3:29])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 69508801HCID 69508801, compound

Product 1

HCID 57526812HCID 57526812, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a mixed solution of tetrahydrofuran (3.2 mL) and water (0.8 mL) containing tert-butyl (S)-3-{6-allyl-7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]pyrazolo[1,5-a]pyrimidin-5-ylamino}piperidine-1-carboxylate (375 mg, 0.632 mmol), sodium periodate (405 mg, 1.89 mmol) and osmium tetraoxide (2.5w/v % tert-butanol solution, 793 μL, 0.063 mmol) were added, and the mixture was stirred. After the reaction, aqueous sodium sulfite was added to the solution, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with brine and dried over sodium sulfate. After the sodium sulfate was filtered off, and the solvent was distilled off to obtain the title compound.

Workup

  1. additionwere added
  2. additionwas added to the solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter the sodium sulfate was filtered off
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-990ca43ffee645f9835d1f8ef2ab86bd
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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