Water → ethyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate

HRID 1943585Notes

Reaction equation

HRID 1943585 reaction equation
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[CH2:21](I)[CH3:22].O>CN(C=O)C>[C:8]([NH:1][C@H:2]([C:5]([O:7][CH2:21][CH3:22])=[O:6])[CH2:3][OH:4])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 13819295ethyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-Ser-OH (0.3 g, 1.46 mmol, 1 eq) in dry DMF (4 ml) at 0° C., dry K2CO3 (0.22 g, 1.6 mmol, 1.1 eq) was added. The resulting white suspension was stirred for 15 minute and ethyl iodide (0.68 g, 0.35 ml, 4.38 mmol, 3 eq) was dropwise added. The cooling was removed and reaction mixture was stirred at room temperature under N2 for 24 h. To the formed white emulsion H2O was added, and the mixture extracted by EtOAc. The combined organic layer was washed by H2O and then brine, and dried over MgSO4. The solvent was evaporated and the obtained oil was dried overnight in high vacuum. Yield of the pure F—0.27 g (79%).

Workup

  1. customThe cooling was removed
  2. customreaction mixture
  3. stirringwas stirred at room temperature under N2 for 24 h
  4. extractionthe mixture extracted by EtOAc
  5. washThe combined organic layer was washed by H2O
  6. dry with materialbrine, and dried over MgSO4
  7. customThe solvent was evaporated
  8. customthe obtained oil was dried overnight in high vacuum

Sources & evidence

ORD record
ord-2a522377b0ac4b24a36933462877dedf
Source dataset
uspto-grants-2013_03
Patent number
US08394790B2

Reaction notes

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