Triethylamine → trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

HRID 362069Notes

Reaction equation

HRID 362069 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C@H:16]([C:32]([OH:34])=[O:33])[CH2:15]1>O1CCCC1>[CH3:8][S:9]([O:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:20])[C@H:16]([C:32]([OH:34])=[O:33])[CH2:15]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 13502650trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12.20 ml of triethylamine and 6.81 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 12.41 g of trans-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline in 100 ml of dry tetrahydrofuran, and the resulting mixture was stirred at the same temperature for 40 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was mixed with 350 ml of ethyl acetate and 50 ml of 1N aqueous hydrochloric acid. The mixture was then stirred at room temperature for 2.5 hours, after which the organic layer was separated and washed three times with an aqueous solution of sodium chloride; it was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, to give 12.57 g of the title compound, as a powder.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. additionthe residue was mixed with 350 ml of ethyl acetate and 50 ml of 1N aqueous hydrochloric acid
  3. stirringThe mixture was then stirred at room temperature for 2.5 hours
  4. customafter which the organic layer was separated
  5. washwashed three times with an aqueous solution of sodium chloride
  6. dry with materialit was then dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1234767b1c9246d28b866a6983c4f67c
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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