Cbz-L-methionine methyl ester → Methyl (2S)-4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]butanoate

HRID 58388Notes

Reaction equation

HRID 58388 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:5][CH2:6][S:7][CH3:8].I([O-])(=O)(=O)=[O:22].[Na+]>CO.O>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:5][CH2:6][S:7]([CH3:8])=[O:22]

Participants

5

Reactant 2

HCID 11141035Cbz-L-methionine methyl esterHCID 23667635Sodium periodate

Product 1

HCID 11077876Methyl (2S)-4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]butanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sulfide 59 (5.40 g, 18.2 mmol) was dissolved in methanol (60 mL). This was cooled in ice and a solution of sodium metaperiodate (4.08 g, 1.05 equiv) in water (25 mL) was added dropwise over 10 mins. This was stirred in ice for 1 h and then at rt for a further 2 h. The resultant white precipitate was removed by filtration under vacuum, the residue washed with methanol and the filtrate concentrated in vacuo. The resultant colourless oil was partitioned between DCM and water. The aqueous phase was extracted twice more with DCM, methanol added to the combined organic extracts to obtain an homogenous solution and this was dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oil, 5.69 g, 100%. This was obtained as a 1:1 mixture of diastereoisomers.

Workup

  1. temperatureThis was cooled in ice
  2. waitat rt for a further 2 h
  3. customThe resultant white precipitate was removed by filtration under vacuum
  4. washthe residue washed with methanol
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resultant colourless oil was partitioned between DCM and water
  7. extractionThe aqueous phase was extracted twice more with DCM, methanol
  8. additionadded to the combined organic extracts
  9. customto obtain an homogenous solution
  10. dry with materialthis was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto afford a yellow oil, 5.69 g, 100%
  14. customThis was obtained as a 1:1 mixture of diastereoisomers

Sources & evidence

ORD record
ord-88162c5164e04310b8468a00853c9bea
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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