Acetic Acid → HCID 57001798, compound

HRID 1638180Notes

Reaction equation

HRID 1638180 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)[C@H:11]([C:21]([O:23][CH3:24])=[O:22])[O:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=[O:29])C>>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:29])=[O:20])=[CH:15][CH:14]=2)[C@H:11]([C:21]([O:23][CH3:24])=[O:22])[O:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 15232290HCID 15232290, compound

Product 1

HCID 57001798HCID 57001798, compound

Conditions

Temperature
45 °C

Procedure

To a solution of 2.1 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-formylphenyl)-5-oxazolidinecarboxylate in 25 cm3 of acetic acid are added 1.06 g of sodium perborate hydrate. The reaction medium is heated with stirring to a temperature in the region of 45° C., maintained for 10 hours at this temperature and then cooled to a temperature in the region of 20° C. and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residual oil is dissolved in 75 cm3 of ethyl acetate and the solution obtained is washed with 5 times 5 cm3 of distilled water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 2.2 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-carboxyphenyl)-5-oxazolidinecarboxylate are thus obtained in the form of a yellow oil.

Workup

  1. temperatureThe reaction medium is heated
  2. temperaturemaintained for 10 hours at this temperature
  3. temperaturecooled to a temperature in the region of 20° C.
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. dissolutionThe residual oil is dissolved in 75 cm3 of ethyl acetate
  6. customthe solution obtained
  7. washis washed with 5 times 5 cm3 of distilled water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-7ed37f00c4344d97ac0b73a9ef200bc5
Source dataset
uspto-grants-2000_03
Patent number
US06043375

Reaction notes

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