2,2-Dimethoxypropane → HCID 58906705, compound

HRID 1870060Notes

Reaction equation

HRID 1870060 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:7])[CH2:5][OH:6].CO[C:19](OC)([CH3:21])[CH3:20].B(F)(F)F.CCOCC>CC(C)=O>[CH3:1][O:2][C:3]([C:4]1([CH3:7])[CH2:5][O:6][C:19]([CH3:21])([CH3:20])[N:8]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:16]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 13221874Methyl 2-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-2-methylpropanoate

Product 1

HCID 58906705HCID 58906705, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of 3 (9.342 g, 40 mmol) in acetone (15 mL) in a flame dried round bottom flask under an inert atmosphere was added 2,2-dimethoxypropane (66 mL). To this solution was added BF3.OEt2 (0.30 mL, cat.) and stirring was continued at room temperature for 2 hours. The reaction mixture was then concentrated in vacuo to an orange oil which was purified by flash chromatography to provide 4 (9.392 g, 85%) as a white solid. Rf=0.55 (1:3 EtOAc/hexanes). Compound was observed as an uneven mixture of rotomers.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo to an orange oil which
  2. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-546c4280f8034a5e8f910ee4085ebbbc
Source dataset
uspto-grants-2009_12
Patent number
US07638637B2

Reaction notes

Loading…