HCID 11199458, compound → HCID 11995331, compound

HRID 2358310Notes

Reaction equation

HRID 2358310 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8](CO)[CH2:9][N:10]1[C:19]([C:20]#[N:21])=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:29][CH3:30])[CH:16]=2)[C:11]1=[O:31]>O.C1COCC1>[F:28][C:24]1[CH:23]=[C:22]([C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:29][CH3:30])[CH:16]=3)[C:11](=[O:31])[N:10]([CH2:9][CH:8]=[O:7])[C:19]=2[C:20]#[N:21])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11199458HCID 11199458, compoundHCID 23667635Sodium periodate

Product 1

HCID 11995331HCID 11995331, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium periodate (368 mg, 1.72 mmol) in water (7 mL) was added to a solution of diol 106 (0.96 mmol) in THF (15 mL) at 0° C. After 7 h an additional 1.8 equivalents of NaIO4 were added. The reaction mixture was stirred overnight then partitioned between EtOAc and NaHCO3. The aqueous phase was extracted with EtOAc and the combined extracts dried (MgSO4). Concentration gave the desired product 107.

Workup

  1. customthen partitioned between EtOAc and NaHCO3
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined extracts dried (MgSO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-355bf4a437c644f7b01809d95ed344c3
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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