Boron trifluoride → HCID 68701831, compound

HRID 1026726Notes

Reaction equation

HRID 1026726 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:11][C:10]=3[F:26])[CH2:5][CH2:4]2)[CH2:2]1.C(O)CCO.B(F)(F)F.[O:36]1[CH2:40]C[CH2:38][CH2:37]1>>[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:11][C:10]=3[F:26])[CH2:5][CH2:4]2)[CH2:38][CH2:37][O:36][CH2:40][CH2:2]1

Participants

5

Reactant 4

HCID 6356Boron trifluorideHCID 8028TetrahydrofuranHCID 104421,3-PropanediolHCID 11382912HCID 11382912, compound

Product 1

HCID 68701831HCID 68701831, compoundYield 51%

Procedure

A mixture of (S)—N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (0.275 mmol), 1,3-propanediol (0.330 mmol) and catalytic amount of BF3.etharate in 10 ml tetrahydrofuran was stirred under reflux for 2 hours. The reaction mixture was evaporated to the dryness under vacuum. The residue obtained was purified on the silica gel column chromatography to provide title compound in 51% yield.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe reaction mixture was evaporated to the dryness under vacuum
  3. customThe residue obtained
  4. customwas purified on the silica gel column chromatography

Sources & evidence

ORD record
ord-b0360f1b33904b5a99f5ef76b012ce9a
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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