Water → HCID 71182912, compound

HRID 1891403Notes

Reaction equation

HRID 1891403 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]=[N+:15]=[N-:16])[O:10][C:9]2=[O:17])[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:22][CH:21]2[CH2:23][C:24]3([CH2:29][CH:20]2[CH2:19]1)[O:28][CH2:27][CH2:26][O:25]3.O.[C:31](OC=C)(=O)[CH3:32]>>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:32]=[CH:31][N:16]=[N:15]3)[O:10][C:9]2=[O:17])[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:22][CH:21]2[CH2:23][C:24]3([CH2:29][CH:20]2[CH2:19]1)[O:28][CH2:27][CH2:26][O:25]3

Participants

4

Reactant 3

HCID 962WaterHCID 7904Vinyl AcetateHCID 71182914HCID 71182914, compound

Product 1

HCID 71182912HCID 71182912, compoundYield 47%

Procedure

5.0 g (12.39 mmol) of 2-[2-fluoro-4-[(5R)-5-(azidomethyl)-2-oxo-3-oxazolidinyl]phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane] prepared in the step 9 of the preparation example 1 was dissolved in 100 ml of vinyl acetate, and the solution was heated to reflux for 30 hours. After the reaction was completed, water was added, and the mixture was extracted with ethyl acetate, and then, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography to obtain 2.5 g (47%) of 2-[2-fluoro-4-[(5R)-5-(1,2,3-triazol-1-ylmethyl)-2-oxo-3-oxazolidinyl]phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane].

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 30 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was separated by column chromatography

Sources & evidence

ORD record
ord-a61fa1d2127a45f8ba8a35e67ee5bffb
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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