Triethylamine → 4-[2-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-2-oxo-ethyl]-piperazine-1-carboxylic Acid Tert-Butyl Ester

HRID 2193546Notes

Reaction equation

HRID 2193546 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.Br[CH2:33][C:34](Br)=[O:35].[C:37]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:40]([O:39][C:37]([N:44]1[CH2:45][CH2:46][N:47]([CH2:33][C:34]([N:11]2[CH2:12][CH2:13][N:8]([C:7]3[CH:6]=[CH:5][C:4]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]4=[O:24])=[CH:3][C:2]=3[F:1])[CH2:9][CH2:10]2)=[O:35])[CH2:48][CH2:49]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10520848(S)-N-((3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Product 1

HCID 672739974-[2-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-2-oxo-ethyl]-piperazine-1-carboxylic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 672 mg of N-[(5S)-3-(3-fluoro-4-piperazine-1-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (2 mmol) and 0.42 ml of triethylamine (3 mmol) in 30 ml dichloromethane was added at rt. a solution of 484 mg bromoacetylbromide (2.4 mmol) in 2 ml of dichloromethane. The reaction was monitored by TLC. The reaction solution was washed with water and brine, the dichloromethane layer dried over Mg sulfate, filtered and the filtrate evaporated to dryness. The residue was digested in 20 ml ether, the solid filtered and dried. The colorless solid was dissolved in 10 ml DMF, 372 mg N-Boc piperazine 2 mmol) and 276 mg of potassium carbonate (2 mmol) were added. The reaction was stirred over night at 60° C. and monitored by TLC. The DMF was evaporated to dryness, the residue purified by chromatography, using a 19/1 dichloromethane/methanol mixture as eluent.

Workup

  1. additionwas added at rt
  2. washThe reaction solution was washed with water and brine
  3. dry with materialthe dichloromethane layer dried over Mg sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. filtrationthe solid filtered
  7. customdried
  8. dissolutionThe colorless solid was dissolved in 10 ml DMF
  9. customThe DMF was evaporated to dryness
  10. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-d6c15481b95c45378508d92d496e130f
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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