Sulfuric Acid → (S)-N-{3-[4-(4-Aminocarbonyl-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 2247023Notes

Reaction equation

HRID 2247023 reaction equation
[C:1]([C:3]1([OH:27])[CH2:8][CH2:7][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])[CH2:5][CH2:4]1)#[N:2].S(=O)(=O)(O)[OH:29]>>[NH2:2][C:1]([C:3]1([OH: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)=[O:29]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 11394757(S)-N-{3-[4-(4-cyano-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Product 1

HCID 11383840(S)-N-{3-[4-(4-Aminocarbonyl-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 62%

Procedure

The compound was obtained by reacting (S)-N-{3-[4-(4-cyano-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (12 mmol) with 95% aqueous sulfuric acid at a temperature 25° C. for 14 hours and purifying the compound by silica gel column chromatography in 62% yield. M.P. 238-40° C. and MS (M+1)=395 (MH+, 100%) for M.F.=C18H23FN4O5.

Workup

  1. customThe compound was obtained
  2. customat a temperature 25° C.
  3. customfor 14 hours
  4. custompurifying the compound by silica gel column chromatography in 62% yield

Sources & evidence

ORD record
ord-d7d0fad1d38643f280c77466104d14c4
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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