Water → HCID 67246684, compound

HRID 1027570Notes

Reaction equation

HRID 1027570 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][O:11][NH:10][C:9]1=[O:13])([CH3:4])([CH3:3])[CH3:2].[CH3:15]C(C)([O-])C.[K+].C(I)I.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]1[CH2:12][O:11][N:10]([CH3:15])[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 5225473HCID 5225473, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67246684HCID 67246684, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(3-Oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester (1.01 g, prepared from (D)-cycloserine as described in Chem. Pharm. Bull. 2002, 50(4) 554-557) was dissolved in dimethylformamide (5 ml), the solution was cooled to 0° C. and 616 mg of potassium t-butoxide was added portionwise. The reaction mixture was stirred at 0° C. for 1 hour then 710 mg methylene iodide was added and the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was then washed several times with water, dried over sodium sulphate and the solvent removed in vacuo. Crude ((R)-2-methyl-3-oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester (140 mg) was obtained as a white solid. LCMS (method A) 1.11 min, MH+ 217; 1H-NMR (CDCl3, 400 MHz): 5.20 (m, 1H), 4.70 (m, 1H), 4.55 (m, 1H), 4.00 (dd, 1H), 3.20 (s, 3H), 1.40 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at room temperature
  2. extractionextracted with diethyl ether
  3. washThe organic phase was then washed several times with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c80f731459da4b1aa870de74e74b6310
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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