2,2-Dimethoxypropane → HCID 58906705, compound

HRID 227561Notes

Reaction equation

HRID 227561 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 (115 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 rt for 2 h. 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-46bfa183463241a79b0f6121132beaee
Source dataset
uspto-grants-2009_07
Patent number
US07560477B2

Reaction notes

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