Triacetoxyperiodinane → HCID 86691729, compound

HRID 1426935Notes

Reaction equation

HRID 1426935 reaction equation
[Cl:1][CH2:2][C@@H:3]([OH:31])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23]([O:29][CH3:30])=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][CH2:2][C:3](=[O:31])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23]([O:29][CH3:30])=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67501462HCID 67501462, compound

Product 1

HCID 86691729HCID 86691729, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((S)-3-chloro-2-hydroxypropyl)-5-((R)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (180 mg, 0.401 mmol) in DCM (3 mL) was added Dess-Martin periodinane (204 mg, 0.481 mmol). The reaction was stirred at ambient temperature for 3 hours, then purified directly by reverse-phase column chromatography, eluting with 5 to 60% acetonitrile/water to yield the desired product as a white foamy solid (114 mg, 64% yield). MS (apci) m/z=447.0 (M+H).

Workup

  1. custompurified directly by reverse-phase column chromatography
  2. washeluting with 5 to 60% acetonitrile/water

Sources & evidence

ORD record
ord-932486d37780464780ee65560262ead1
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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