Dimethylformamide → (2S,4R)-2-(4-carbamoylthiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1649827Notes

Reaction equation

HRID 1649827 reaction equation
C[N:2](C)C=O.P(Cl)(Cl)(Cl)=O.[C:11]([C:14]1[N:15]=[C:16]([C@@H:19]2[CH2:23][C@@H:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:21][N:20]2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[S:17][CH:18]=1)([OH:13])=O.O.N>O1CCCC1>[C:11]([C:14]1[N:15]=[C:16]([C@@H:19]2[CH2:23][C@@H:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:21][N:20]2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[S:17][CH:18]=1)(=[O:13])[NH2:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12896473Azane;hydrateHCID 18638791(2S,4R)-2-(4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

Product 1

HCID 57324351(2S,4R)-2-(4-carbamoylthiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of dimethylformamide (0.45 ml) and tetrahydrofuran (10 ml) was dropwise added phosphorus oxychloride (0.46 ml) at -5°~5° C., and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2-(4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.54 g) in tetrahydrofuran (20 ml) at -5°~5° C., followed by stirring at the same temperature for 30 minutes. The mixture was dropwise added to concentrated ammonia water (15 ml) at 0°-10° C. with stirring. The mixture was stirred at the same condition for 2 hours. Tetrahydrofuran was removed under reduced pressure to give a residue, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give (2S,4R)-2-(4-carbamoylthiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.4 g).

Workup

  1. customat -5°~5° C.
  2. stirringby stirring at the same temperature for 30 minutes
  3. stirringwith stirring
  4. stirringThe mixture was stirred at the same condition for 2 hours
  5. customTetrahydrofuran was removed under reduced pressure
  6. customto give a residue, which
  7. extractionwas extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef1ab8a2a3d4c4bbd1590e603e60a11
Source dataset
uspto-grants-1990_05
Patent number
US04921852

Reaction notes

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