Sodium Thiosulfate → methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

HRID 869727Notes

Reaction equation

HRID 869727 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([O:20][CH3:21])=[O:19])[C@@H:15]([CH3:17])[OH:16])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@@H:14]([C:15](=[O:16])[CH3:17])[C:18]([O:20][CH3:21])=[O:19])=[O:12])[CH3:10])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11483528methyl N-(tert-butoxycarbonyl)-L-alanyl-L-threoninate

Product 1

HCID 86674523methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-L-alanyl-L-threoninate (9.00 g, 29.6 mmol) in dichloromethane (90 mL) was added Dess-Martin periodinane (15.1 g, 35.5 mmol) at room temperature. After being stirred for 70 min, saturated aqueous sodium thiosulfate solution was added, then the reaction mixture was stirred for 15 min. The mixture was poured into saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to give methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate. MS (APCI): m/z 303 (M+H).

Workup

  1. stirringthe reaction mixture was stirred for 15 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-2b6f12c30d794535bc581ed5f5fa7e7e
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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