Pyridine → HCID 68972378, compound

HRID 2197654Notes

Reaction equation

HRID 2197654 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>C1(C)C=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

6

Reactant 4

HCID 1049PyridineHCID 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 1140TolueneSolvent

Conditions

Temperature
82.5 °C

Procedure

(1S,2S)-(2-hydroxy-1-phenyl-but-3-enyl)-carbamic acid tert-butyl ester (160 grams, 0.608 mole) was dissolved in toluene (1600 mL). Dimethoxypropane (745 mL, 6.08 mole) was added at temperature in the range of 20-40° C. followed by addition of pyridinium p-toluene sulphonate (2.3 grams, 0.00912 mole). The mixture was heated to 80-85° C., and stirred at the same temperature for about 2-3 hours. The reaction mixture was cooled to 45° C., neutralized with pyridine (3 mL), and concentrated under reduced pressure to get the semi-solid compound (4S,5R)-2,2-dimethyl-4-phenyl-5-vinyl-oxazolidine-3-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe reaction mixture was cooled to 45° C.
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48cd7a9d2fa841ebbfac189a7976abdd
Source dataset
uspto-grants-2012_12
Patent number
US08338617B2

Reaction notes

Loading…