Acetic Acid → 9-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic Acid

HRID 2193537Notes

Reaction equation

HRID 2193537 reaction equation
C([O:3][C:4]([C:6]1[C:17](=[O:18])[C:16]2[C:19]3[N:8]([N:9]([CH3:45])[CH2:10][O:11][C:12]=3[C:13]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([N:33]5[CH2:37][C@H:36]([CH2:38][NH:39][C:40](=[O:42])[CH3:41])[O:35][C:34]5=[O:43])=[CH:29][C:28]=4[F:44])[CH2:23][CH2:22]3)=[C:14]([F:20])[CH:15]=2)[CH:7]=1)=[O:5])C.Cl.C(O)(=O)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:40]([NH:39][CH2:38][C@@H:36]1[O:35][C:34](=[O:43])[N:33]([C:30]2[CH:31]=[CH:32][C:27]([N:24]3[CH2:23][CH2:22][N:21]([C:13]4[C:12]5=[C:19]6[C:16]([C:17](=[O:18])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]6[N:9]([CH3:45])[CH2:10][O:11]5)=[CH:15][C:14]=4[F:20])[CH2:26][CH2:25]3)=[C:28]([F:44])[CH:29]=2)[CH2:37]1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 672742189-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic Acid Ethyl Ester

Product 1

HCID 101888699-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

44 mg of 9-(4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic acid ethyl ester (0.32 mmol) were heated at 80° C. in 2 ml of a 1/1 conc. HCl and acetic acid mixture. The reaction was monitored by HPLC. The HCl/AcOH mixture was evaporated, the residue dissolved in a methanol/dichloromethane 1/1 mixture, treated with triethylamine and evaporated. The deacetylated residue was dissolved in a 1/1 mixture acetic acid and acetic anhydride, and the reaction monitored by HPLC. The solvents were evaporated and the residue was purified by preparative HPLC.

Workup

  1. customThe HCl/AcOH mixture was evaporated
  2. dissolutionthe residue dissolved in a methanol/dichloromethane 1/1 mixture
  3. additiontreated with triethylamine
  4. customevaporated
  5. dissolutionThe deacetylated residue was dissolved in a 1/1 mixture acetic acid and acetic anhydride
  6. customThe solvents were evaporated
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b8a71deaf12b47bfb4d82a4773f5eb2d
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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