Sodium Chloride → (2S,4R)-1-allyloxycarbonyl-2-carboxy-4-hydroxypyrrolidine

HRID 1090502Notes

Reaction equation

HRID 1090502 reaction equation
[C:1]([C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][NH:5]1)([OH:3])=[O:2].Cl[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12].[OH-].[Na+].[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[CH2:14]([O:13][C:11]([N:5]1[CH2:6][C@H:7]([OH:9])[CH2:8][C@H:4]1[C:1]([OH:3])=[O:2])=[O:12])[CH:15]=[CH2:16]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 5810L-HydroxyprolineHCID 14798Sodium HydroxideHCID 18052Allyl chloroformate

Product 1

HCID 18639171(2S,4R)-1-allyloxycarbonyl-2-carboxy-4-hydroxypyrrolidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (2S,4R)-2-carboxy-4-hydroxypyrrolidine (300 g) in a mixture of tetrahydrofuran (1.5 l) and water (1.5 l) was added dropwise a solution of allyl chloroformate (292 ml) in tetrahydrofuran (300 ml) at 0° C. while adjusting pH to around 9 with 4N aqueous sodium hydroxide. After stirring at 0° C. for 1 hour at pH 9, the aqueous layer was saturated with sodium chloride, and the mixture was diluted with ethyl acetate (1 l). The aqueous layer was separated, washed with ethyl acetate (1 l). After adjusting pH to around 2 with 12N hydrochloric acid, the emulsion was extracted with two portions of ethyl acetate (1 l×2). The combined extract was dried over magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-carboxy-4-hydroxypyrrolidine (426.2 g)

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate (1 l)
  3. extractionthe emulsion was extracted with two portions of ethyl acetate (1 l×2)
  4. extractionThe combined extract
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8c312ec966f64ca988fe4d62d487370a
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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