2,2-Dimethoxypropane → HCID 68972378, compound

HRID 2197652Notes

Reaction equation

HRID 2197652 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:9]([OH:12])[CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].CO[C:22](OC)([CH3:24])[CH3:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:7]1[C@@H:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([CH:10]=[CH2:11])[O:12][C:22]1([CH3:24])[CH3:23])=[O:19])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10084124HCID 10084124, compound

Product 1

HCID 68972378HCID 68972378, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
82.5 °C

Procedure

(1S,2S)-(2-hydroxy-1-phenyl-but-3-enyl)carbamic acid t-butyl ester is dissolved in an aromatic solvent. 2,2-Dimethoxypropane is added at a temperature in the range of about 20-40° C. followed by addition of pyridinium p-toluene sulfonate. The reaction mixture is heated to about 70-95° C. and stirred at the same temperature for about 1-5 hours. The reaction mixture is cooled to about 30 to 45° C., neutralized with pyridine, and concentrated under reduced pressure to get (4S,5R)-2,2-dimethyl-4-phenyl-5-vinyl-oxazolidine-3-carboxylic acid t-butyl ester in a semi solid form, which is optionally further purified by column chromatography, such as using petroleum ether and ethyl acetate as solvents.

Workup

  1. temperatureThe reaction mixture is cooled to about 30 to 45° C.
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-856254cedeea4682a89779015aa5e54e
Source dataset
uspto-grants-2012_12
Patent number
US08338617B2

Reaction notes

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