(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid → Ethyl(2s)-2-[(4s)-4-methyl-2-oxido-5-oxo-1,2,3-oxathiazolidin-3-yl]-pentanoate

HRID 349411Notes

Reaction equation

HRID 349411 reaction equation
[CH3:1][CH2:2][CH2:3][C@H:4]([NH:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].N1([S:21](Cl)=[O:22])C=CN=C1>ClCCl>[CH3:12][C@H:11]1[C:13](=[O:15])[O:14][S:21](=[O:22])[N:10]1[C@@H:4]([CH2:3][CH2:2][CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acidHCID 113325591H-Imidazole-1-sulfinyl chloride

Product 1

HCID 11242493Ethyl(2s)-2-[(4s)-4-methyl-2-oxido-5-oxo-1,2,3-oxathiazolidin-3-yl]-pentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Introduce into a reactor 200 g of N-[(S)-ethoxycarbonyl-1-butyl]-(S)-alanine and 1.5 liters of dichloromethane and then, at 0° C., add 325 g of 1H-imidazole-1-sulphinyl chloride. Subsequently, bring the reaction mixture to ambient temperature and then, after stirring for 1 hour, filter off the precipitate formed. The filtrate obtained is evaporated to dryness to yield the expected product in the form of an oil.

Workup

  1. customto ambient temperature
  2. filtrationfilter off the precipitate
  3. customformed
  4. customThe filtrate obtained
  5. customis evaporated to dryness

Sources & evidence

ORD record
ord-8480382943764e6d9946aa05c1ece591
Source dataset
uspto-grants-2007_02
Patent number
US07179833B2

Reaction notes

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