Sodium Chloride → (2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine

HRID 1030159Notes

Reaction equation

HRID 1030159 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:15]1[C:20]([OH:22])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH2:23]([NH2:25])[CH3:24].[Cl-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:15]1[C:20](=[O:22])[NH:25][CH2:23][CH3:24])=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6341EthylamineHCID 10928Ethyl chloroformateHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 57061747(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

15.25 ml of triethylamine and subsequently a solution of 10.48 ml of ethyl chloroformate in 50 ml of dry tetrahydrofuran were added at -25° C. to a solution of 23.13 g of (2S, 4S)-1-t-butoxycarbonyl-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 350 ml of dry tetrahydrofuran, and the mixture was stirred at the same temperature for 30 minutes. At the end of this time, a 70% by volume aqueous ethylamine solution was added at -22° C., the reaction temperature was allowed to rise gradually and the reaction finished when the temperature reached 10° C. The reaction mixture was then mixed with a small amount of an aqueous solution of sodium chloride, after which it was extracted thrice with ethyl acetate. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 23.60 g of the title compound as a colorless oil.

Workup

  1. customreached 10° C
  2. extractionafter which it was extracted thrice with ethyl acetate
  3. washThe combined extracts were washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-d5b64e2be328424d8d3473458734d47c
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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