Boron trifluoride → HCID 11212006, compound

HRID 1026715Notes

Reaction equation

HRID 1026715 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[SH:26][CH:27](O)[CH3:28].B(F)(F)F>O1CCCC1>[S:26]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]4=[O:24])=[CH:10][C:9]=3[F:25])[CH2:6][CH2:7]2)[O:1][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 4713212Mercapto-ethanolHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 11212006HCID 11212006, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.86 mmol), mercaptoethanol (3.15 mmol) and BF3 etherate (5.14 mmol) in 10 ml tetrahydrofuran was heated under reflux for 6 hours. The solvent was evaporated and the residue was extracted with ethyl acetate water mixture the organic layer was concentrated and the crude residue was purified on a silica gel column to afford the titled compound in 85% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was evaporated
  4. extractionthe residue was extracted with ethyl acetate water mixture the organic layer
  5. concentrationwas concentrated
  6. customthe crude residue was purified on a silica gel column

Sources & evidence

ORD record
ord-854170c3b11643a69e74487e0238b482
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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