Acetic Acid → HCID 59218576, compound

HRID 1026734Notes

Reaction equation

HRID 1026734 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[C:14]([F:15])=[CH:13][C:12]([N:16]4[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]4=[O:26])=[CH:11][C:10]=3[F:27])[CH2:5][CH2:4]2)[CH2:2]1.[N-:28]=[N+:29]=[N-:30].[Na+].C(O)(=O)C>CN(C)C=O>[N:28]([CH2:2][C:3]1([OH:1])[CH2:8][CH2:7][N:6]([C:9]2[C:14]([F:15])=[CH:13][C:12]([N:16]3[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]3=[O:26])=[CH:11][C:10]=2[F:27])[CH2:5][CH2:4]1)=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 59226623HCID 59226623, compound

Product 1

HCID 59218576HCID 59218576, compoundYield 65%

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)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.30 mmol) with sodium azide (2.10 mmol) and glacial acetic acid (7.0 mmol) in dimethylformamide (15 ml) at a temperature 40° C. for 14 hours and by purifying the compound by silica gel column chromatography in 65% yield.

Workup

  1. customat a temperature 40° C.
  2. customfor 14 hours
  3. customby purifying the compound by silica gel column chromatography in 65% yield

Sources & evidence

ORD record
ord-409dc41d979e49dca0b069214a1bea41
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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