HCID 15382966, compound → HCID 86711285, compound

HRID 336149Notes

Reaction equation

HRID 336149 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[OH:7][CH2:8][CH2:9][C@@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:12][S:13][CH3:14]>O.CO>[OH:7][CH2:8][CH2:9][C@@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:11][CH2:12][S:13]([CH3:14])=[O:2]

Participants

5

Reactant 2

HCID 15382966HCID 15382966, compoundHCID 23667635Sodium periodate

Product 1

HCID 86711285HCID 86711285, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of sodium periodate (7.0 g) in water (32 ml) was added to a solution of (R)-tert-butyl (1-hydroxy-5-(methylthio)pentan-3-yl)carbamate (8.16 g) obtained in Step 1 in methanol (98 ml) at a temperature 10° C. or lower, and the mixture was stirred at room temperature for 2 hours. The generated insoluble matter was filtered off, and the filtrate was distilled off under reduced pressure. The resulting residue was dissolved in a saturated sodium chloride solution, followed by extraction with chloroform for 3 times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as a light-yellow solid (9.38 g).

Workup

  1. filtrationThe generated insoluble matter was filtered off
  2. distillationthe filtrate was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in a saturated sodium chloride solution
  4. extractionfollowed by extraction with chloroform for 3 times
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fb019be9e77540a593644c3d26b0b2a3
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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