Sodium Iodide → HCID 68701493, compound

HRID 2247015Notes

Reaction equation

HRID 2247015 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.[I-:27].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[OH:1][C:3]1([CH2:2][I:27])[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:11][C:10]=2[F:26])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 11382912HCID 11382912, compound

Product 1

HCID 68701493HCID 68701493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (10.0 mmol) and sodium iodide (11.0 mmol) in presence of catalytic p-toluene sulfonic acid in dimethyl formamide at a temperature 50-60° C. for 12 hours to provide crude (S)-N-{3-[4-(4-hydroxy-4-iodomethylpiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide which was purified by silica gel column chromatography and used further.

Sources & evidence

ORD record
ord-30f616b7926d4d80881d17a9f94118ef
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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