Triethylamine → HCID 54482710, compound

HRID 620779Notes

Reaction equation

HRID 620779 reaction equation
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:21][C@H:20]1[CH2:29][O:30][CH2:31][C:32]([OH:34])=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:37](CC)CC)C.O.N>O1CCCC1>[CH2:9]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:21][C@H:20]1[CH2:29][O:30][CH2:31][C:32](=[O:34])[NH2:37])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 12896473Azane;hydrateHCID 54131619HCID 54131619, compound

Product 1

HCID 54482710HCID 54482710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of isobutyl chloroformate (9 ml) in tetrahydrofuran (20 ml) was dropwise added to a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxymethyloxymethyl-4-methanesulfonyloxypyrrolidine (24.85 g) and triethylamine (10.75 ml) in tetrahydrofuran (120 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 (250 ml) at 0°-5° C. and the solution was stirred at the same temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with water (200 ml×3), 1N hydrochloric acid (300 ml×2), saturated sodium hydrogen carbonate (300 ml) and brine in turn, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (250 g) and eluted with a mixture of methanol and chloroform (2:98 and then 4:96 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-carbamoylmethyloxymethyl-4-methanesulfonyloxypyrrolidine (15.52 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 30 minutes
  2. extractionThe reaction mixture was extracted with ethyl acetate (300 ml)
  3. washThe organic layer was washed with water (200 ml×3), 1N hydrochloric acid (300 ml×2), saturated sodium hydrogen carbonate (300 ml) and brine in turn
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of methanol and chloroform (2:98

Sources & evidence

ORD record
ord-84487c694bfb477f93a5b1bdc924363c
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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