Triethylamine → (2S, 4R)-2-(carbamoylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 620773Notes

Reaction equation

HRID 620773 reaction equation
ClC(OCC(C)C)=O.[C:9]([CH2:12][O:13][CH2:14][C@@H:15]1[CH2:19][C@@H:18]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][N:16]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:26])(O)=[O:10].C([N:40](CC)CC)C.O.N>O1CCCC1.O>[C:9]([CH2:12][O:13][CH2:14][C@@H:15]1[CH2:19][C@@H:18]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][N:16]1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=1)=[O:26])(=[O:10])[NH2:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 12896473Azane;hydrateHCID 18631935(2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18641549(2S, 4R)-2-(carbamoylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isobutyl chloroformate (0.60 g) in tetrahydrofuran (1 ml) was dropwise added to a solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.28 g) and triethylamine (0.82 ml) in tetrahydrofuran (13 ml) at -10°~-5° C. and the mixture was stirred at the same temperature for 30 minutes. The mixture was dropwise added to concentrated ammonia water (10 ml) at 0°-5° C. and the solution was stirred at the same temperature for 1 hour. The mixture was poured into water (50 ml) and extracted with chloroform (50 ml). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatogaraphy on silica gel (25 g) and eluted with a mixture of methanol and chloroform (2:98 V/V) to give (2S,4R)-2-(carbamoylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.00 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 1 hour
  2. extractionextracted with chloroform (50 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and chloroform (2:98 V/V)

Sources & evidence

ORD record
ord-942eea267d834a598143e774a1ffcf31
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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