Sodium periodate → HCID 86607425, compound

HRID 1178336Notes

Reaction equation

HRID 1178336 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)([CH2:15][NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH2:10][CH:11]([OH:14])CO)[CH3:8])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[C:1]([O:5][C:6](=[O:30])[N:7]([C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)([CH2:15][NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH2:10][CH:11]=[O:14])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86607426HCID 86607426, compound

Product 1

HCID 86607425HCID 86607425, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl{1-(3,4-dichlorophenyl)-3,4-dihydroxy-1-[(methylpropionylamino)-methyl]-butyl}-methyl-carbamate (1.09 g) was dissolved in a mixture solvent of tetrahydrofuran (8 mL) and water (8 mL). Sodium periodate (1.0 g) was added thereto, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby give the title compound (1.05 g, quantative amount). The compound was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4072002fe1fd4f70a1cc4e2249c73730
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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