Hydrochloric Acid → (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate

HRID 1056114Notes

Reaction equation

HRID 1056114 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([C@@H:13]([CH3:15])[OH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CC1C=CC=C(C)N=1.FC(F)(F)S(O[Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])(=O)=O.Cl>C(Cl)Cl>[C:9]([O:8][C:6]([NH:5][C@@H:4]([C@H:13]([O:14][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:15])[C:3]([O:2][CH3:1])=[O:16])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11368286Methyl N-(tert-butoxycarbonyl)-L-threoninate

Product 1

HCID 11824217(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-L-threonine methyl ester (Aldrich) (717 mg, 3.07 mmol) in DCM (10 mL) was cooled in an ice-water bath and treated with 2,6-dimethylpyridine (Aldrich) (1.07 mL, 9.22 mmol) followed by tert-butyldimethylsilyl trifluoromethanesulfonate (Fluka) (0.85 mL, 3.69 mmol). The solution was stirred for 16 h, poured into 1 M aq. HCl (100 mL), and extracted with DCM (2×50 mL). The organic extracts were washed with saturated aq. NaHCO3 (100 mL), dried (MgSO4), filtered, and concentrated to give (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (614a) (1.07 g, 3.08 mmol, 100% yield) as a colorless oil.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe organic extracts were washed with saturated aq. NaHCO3 (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09bad29c491c400db064c0e07cc28435
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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