Acetic Acid → HCID 11246760, compound

HRID 1026676Notes

Reaction equation

HRID 1026676 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.[N-:27]=[N+:28]=[N-:29].[Na+].C(O)(=O)C>CN(C)C=O>[N:27]([CH2:2][C:3]1([OH:1])[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)=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 11382912HCID 11382912, compound

Product 1

HCID 11246760HCID 11246760, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (1.37 mmol) with sodium azide (2.06 mmol) and glacial acetic acid (7.1 mmol) in dimethylformamide (15 ml) at a temperature 40° C. for 14 hours and by purifying the compound by silica gel column chromatography in 72% yield.

Workup

  1. customat a temperature 40° C.
  2. customfor 14 hours
  3. customby purifying the compound by silica gel column chromatography in 72% yield

Sources & evidence

ORD record
ord-6e101625207845ff99d79fda1aab3ad3
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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