Potassium Carbonate → 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)oxetane-3-carboxylic acid

HRID 2046559Notes

Reaction equation

HRID 2046559 reaction equation
[C:1](=O)([O:17]N1C(=O)CCC1=O)[O:2][CH2:3][CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.[NH2:26][C:27]1([C:31]([OH:33])=[O:32])[CH2:30][O:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH:15]1[C:16]2[CH:4]([CH2:3][O:2][C:1]([NH:26][C:27]3([C:31]([OH:33])=[O:32])[CH2:30][O:29][CH2:28]3)=[O:17])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 150242563-Aminooxetane-3-carboxylic acid

Product 1

HCID 679511683-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)oxetane-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate (3.2 g, 9.5 mmol) in dioxane (30 ml) was added to a solution of 3-amino-oxetane-3-carboxylic acid (1.17 g, mmol) and potassium carbonate (2.76 g, 20.0 mmol) in water (30 ml). The light yellow opaque solution was stirred at room temperature for 75 minutes. During that time, a white solid precipitated. The mixture was diluted with water and extracted two times with diethyl ether. The white solid did not dissolve and was kept therefore in the aqueous layer, which was acidified to pH 2 by addition of 1N HCl and extracted three times with EtOAc. The combined EtOAc layers were washed with brine, dried with Na2SO4 and evaporated. The crude title compound was obtained as white solid and was used without further purification.

Workup

  1. customDuring that time, a white solid precipitated
  2. additionThe mixture was diluted with water
  3. extractionextracted two times with diethyl ether
  4. dissolutionThe white solid did not dissolve
  5. additionin the aqueous layer, which was acidified to pH 2 by addition of 1N HCl
  6. extractionextracted three times with EtOAc
  7. washThe combined EtOAc layers were washed with brine
  8. dry with materialdried with Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-3649eb7ad7e3440fa1fe87e48237d652
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

Loading…