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Dimethylformamide → (2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 703574
Notes
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Reaction equation

HRID 703574 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.C([CH2:14][O:15][CH2:16][C@@H:17]1[CH2:21][C@@H:20]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:19][N:18]1[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28])(O)=O.Cl.CNC>O1CCCC1.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][N:2]([CH3:5])[C:3]([CH2:14][O:15][CH2:16][C@@H:17]1[CH2:21][C@@H:20]([O:22][S:23]([CH3:26])(=[O:24])=[O:25])[CH2:19][N:18]1[C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=1)=[O:28])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 10473Dimethylamine, hydrochlorideHCID 24813Phosphorus oxychlorideHCID 18631935(2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 86744485(2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of dimethylformamide (3.9 ml) and tetrahydrofuran (30 ml) was dropwise added phosphorus oxychloride (3.75 ml) at 0°-10° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (14.50 g) in tetrahydrofuran (15 ml) at 0°-10° C. and the mixture was stirred at the same temperature for 30 minutes. The resulting mixture was dropwise added to a mixture of dimethylamine hydrochloride (50 g) and triethylamine (100 ml) in methanol (200 ml) at 0°-10° C. with stirring. The mixture was stirred at the same temperature for 2 hours. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. The syrup was dissolved in ethyl acetate (200 ml), washed with water (200 ml), 1N hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and brine (200 ml), in turn, dried over magnesium sulfate, and concentrated under reduced pressure to give (2S,4R)-2-(dimethylcarbamoyl)methyloxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (12.03 g).

Workup

  1. customat 0°-10° C.
  2. stirringthe mixture was stirred at the same temperature for 30 minutes
  3. stirringwith stirring
  4. stirringThe mixture was stirred at the same temperature for 2 hours
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto give a syrup
  8. washwashed with water (200 ml), 1N hydrochloric acid (200 ml), saturated aqueous sodium hydrogen carbonate (200 ml) and brine (200 ml), in turn
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3b3e852e32047a486dd1f0df75fbe4e
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04983596

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes