Water → (S)-N-Fmoc-azetidine-2-carboxylic acid

HRID 344655Notes

Reaction equation

HRID 344655 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16].O>O1CCOCC1>[CH:30]1[C:31]2[CH:19]([CH2:18][O:17][C:15]([N:1]3[CH2:4][CH2:3][C@H:2]3[C:5]([OH:7])=[O:6])=[O:16])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 16486L-Azetidine-2-carboxylic acidHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 2734468(S)-N-Fmoc-azetidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.50 g of (S)-(-)-2-azetidine carboxylic acid in 15 ml of 10 aqueous sodium carbonate solution was added 1.3 g of 9-fluorenylmethyl chloroformate in 10 ml of dioxane, dropwise, while maintaining the temperature of the reaction mixture at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 3 hours, then poured into water and the aqueous solution was washed with ether. The aqueous layer was cooled to 0° C. and adjusted to a pH of 2 with 3N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, filtered, and evaporated in vacuo to give (S)-N-(9-fluorenylmethoxycarbonyl) azetidine-2-carboxylic acid.

Workup

  1. temperatureto warm to room temperature
  2. washthe aqueous solution was washed with ether
  3. temperatureThe aqueous layer was cooled to 0° C.
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-09b5fa75c0ab42bc8df7bc139deaeb65
Source dataset
uspto-grants-1991_10
Patent number
US05053392

Reaction notes

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