Water → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 371218Notes

Reaction equation

HRID 371218 reaction equation
C(OC([NH:11][C@H:12]([C:16]([NH2:18])=[O:17])[C@@H:13]([CH3:15])O)=O)C1C=CC=CC=1.C[S:20](Cl)(=[O:22])=[O:21].[OH2:24]>N1C=CC=CC=1>[NH2:11][C@H:12]1[C@H:13]([CH3:15])[N:18]([S:20]([OH:22])(=[O:24])=[O:21])[C:16]1=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chloride2×HCID 7010574Phenylmethyl N-((1S,2R)-1-(aminocarbonyl)-2-hydroxypropyl)carbamate

Product 1

HCID 133361(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an atmosphere of argon, 100 g of benzyloxycarbonylthreonine amide is dissolved in 400 ml of anhydrous pyridine and cooled in an ice/salt bath. To this stirring solution, 36.8 ml (54.5 g) of methanesulfonyl chloride is added over a 15 minute period. After 2 hours of stirring an additional 0.3 equivalents of methanesulfonyl chloride is added. The reaction is then stirred for 1 hour and poured into a mixture of 1.5 l of ice and 2 l of water. The resulting slurry is stirred for about 30 minutes and filtered. Drying of the crude product at 60° C. for about 16 hours in a vacuum oven gives 109 g of the title compound.

Workup

  1. temperaturecooled in an ice/salt bath
  2. additionis added
  3. stirringThe resulting slurry is stirred for about 30 minutes
  4. filtrationfiltered
  5. dry with materialDrying of the crude product at 60° C. for about 16 hours in a vacuum oven

Sources & evidence

ORD record
ord-1959313ce0d54bfa91fc34b5bcec4813
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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