2,2-Dimethoxypropane → 3-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

HRID 1295523Notes

Reaction equation

HRID 1295523 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].CO[C:18](OC)([CH3:20])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][O:6][C:18]([CH3:20])([CH3:19])[N:7]1[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])=[O:15]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 495564Methyl N-(tert-butoxycarbonyl)serinateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 51384973-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (34) in CH2Cl2 stirring under nitrogen at 0° C., was added 2,2-dimethoxypropane (29,5 mL, 237.9 mmol) and p-toluene sulfonic acid monohydrate (9.050 g, 47.58 mmol). The mixture was removed from the ice bath after 15 minutes and stirred at room temperature for 1.5 hours. The reaction mixture was poured into 50 mL of saturated NaHCO3 (aq) and extracted with diethyl ether (3×50). The organic layer was extracted with NaHCO3 and brine, then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on SiO2 (1:1 EtOAc/Hexanes) to yield 7.659 g (62%, 3 steps) of a clear liquid.

Workup

  1. customThe mixture was removed from the ice bath after 15 minutes
  2. additionThe reaction mixture was poured into 50 mL of saturated NaHCO3 (aq)
  3. extractionextracted with diethyl ether (3×50)
  4. extractionThe organic layer was extracted with NaHCO3 and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on SiO2 (1:1 EtOAc/Hexanes)
  9. customto yield 7.659 g (62%, 3 steps) of a clear liquid

Sources & evidence

ORD record
ord-5ecce35de3c244468ee0c90fdc991478
Source dataset
uspto-grants-2007_07
Patent number
US07241790B2

Reaction notes

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