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Dimethylformamide → Tetrabutylammonium (2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate

HRID 371215
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 371215
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:15]([CH3:16])[NH:14][C:13]1=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18](=[O:21])(=[O:20])=[O:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:30][N:31]([CH3:34])[CH:32]=O>>[CH2:30]([N+:31]([CH2:34][CH2:13][CH2:12][CH3:15])([CH2:16][CH2:15][CH2:12][CH3:13])[CH2:32][CH2:4][CH2:5][CH3:6])[CH2:1][CH2:2][CH3:3].[CH3:16][C@@H:15]1[N:14]([S:18]([O-:21])(=[O:20])=[O:19])[C:13](=[O:17])[C@H:12]1[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]
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Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 24682Sulfur trioxideHCID 62657Potassium Phosphate, TribasicHCID 13182463(3S-trans)-3-Benzyloxycarbonylamino-4-methylazetidinone

Produkt 1

HCID 13631608Tetrabutylammonium (2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate

Versuchsvorschrift

A solution of 600 mg of (3S-trans)-3-benzyloxycarbonylamino-4-methylazetidinone in 2 ml of dimethylformamide is cooled to 0° C. and 4 ml of 0.8M sulfur trioxide in dimethylformamide is added. The solution is stirred at room temperature under nitrogen for 1 hour and poured into 80 ml of cold 0.5M monobasic potassium phosphate (adjusted to pH 5.5). The solution is extracted with three 50 ml portions of methylene chloride (discarded) and 868 mg of tetrabutylammonium bisulfate is added. The resulting solution is extracted with four 75 ml portions of methylene chloride. The combined organic layer is washed with 8% aqueous sodium chloride, dried, and evaporated in vacuo yielding 1.54 g of the title compound.

Aufarbeitung

  1. extractionThe solution is extracted with three 50 ml portions of methylene chloride (discarded) and 868 mg of tetrabutylammonium bisulfate
  2. additionis added
  3. extractionThe resulting solution is extracted with four 75 ml portions of methylene chloride
  4. washThe combined organic layer is washed with 8% aqueous sodium chloride
  5. customdried
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-074ef26fcc2f4838b3808cf015162527
Quelldatensatz
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04529698

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