Boron trifluoride → HCID 60133520, compound

HRID 2247074Notes

Reaction equation

HRID 2247074 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.[SH:27][CH2:28][CH2:29][CH2:30]O.B(F)(F)F>>[O:1]1[C:3]2([CH2:4][CH2:5][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])[CH2:7][CH2:8]2)[CH2:2][S:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 3

HCID 6356Boron trifluorideHCID 882113-MercaptopropanolHCID 11382912HCID 11382912, compound

Product 1

HCID 60133520HCID 60133520, compound

Procedure

The title compound was prepared by reacting (S)-N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (0.3 mmol) with 3-mercaptopropanol (0.36 mmol), BF3.etherate (catalytic) in tetrahydrofuran (10 ml) at 70-80° C. for 14 hours followed by silica gel column chromatographic purification to provide title compound in 48% yield.

Workup

  1. customThe title compound was prepared
  2. custometherate (catalytic) in tetrahydrofuran (10 ml) at 70-80° C. for 14 hours followed by silica gel column chromatographic purification

Sources & evidence

ORD record
ord-fc0c1320633c45d9b829549bcc372fbe
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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