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

HRID 973538Notes

Reaction equation

HRID 973538 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([OH:7])=[O:6].[CH:8]1[C:20]2[CH:19]([CH2:21][O:22][C:23](Cl)=[O:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1.O>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[CH:8]1[C:20]2[CH:19]([CH2:21][O:22][C:23]([N:1]3[CH2:4][CH2:3][C@H:2]3[C:5]([OH:7])=[O:6])=[O:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 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-fluorenylmethylchloroformate 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 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 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-6e5b12d11c9f4bd4bb971119c3bdbb37
Source dataset
uspto-grants-1991_11
Patent number
US05064814

Reaction notes

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