Acetic Anhydride → Linezolid

HRID 15257

Reaction equation

HRID 15257 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH2:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(OC(=O)C)C>[CH3:23][C:22]([NH:20][CH2:19][C@@H:17]1[O:16][C:15](=[O:21])[N:14]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[C:2]([F:1])[CH:3]=2)[CH2:18]1)=[O:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

Product 1

HCID 441401Linezolid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of (S)—N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine (10 gm) and ethylacetate (100 ml), acetic anhydride (10 ml) is slowly added at ambient temperature, then stirred at ambient temperature for 1 hour. The separated solid is filtered and dried under reduced pressure at 50° C. to give 9.5 gm of linezolid form III.

Workup

  1. additionis slowly added at ambient temperature
  2. filtrationThe separated solid is filtered
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-cc8a9fcd38c64c68973cc27bcdf0eef9
Source dataset
uspto-grants-2010_06
Patent number
US07732597B2

Linked notes

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