2-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)- → (+)-(S)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

HRID 372167Notes

Reaction equation

HRID 372167 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:19][CH2:18]3)[C:6]=2[CH:31]=1.O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C@H:7]([N:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:21][CH2:22]3)[C:6]=2[CH:31]=1

Participants

4

Reactant 2

HCID 30425092-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)-HCID 1226536210-Camphorsulfonic acid monohydrate

Product 1

HCID 3042544(+)-(S)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinoneYield 23.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

3 G. of the salt of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone with (+)-camphor-10-sulfonic acid monohydrate [(S)-2-oxo-10-bornanesulfonic acid; α546 = +28.0° (water; c = 10%)] in the molar ratio of 1:2 are dissolved in 5 ml. of acetone and allowed to stand at room temperature for 2 hours. After the addition of 5 ml. of acetone, the entire mixture is allowed to stand for an additional 2 hours and then treated with 3 ml. of acetone. The solution is now left to stand at room temperature for 85 hours. The precipitate obtained is subsequently removed by filtration and washed with acetone, and there is obtained the di(camphor-10-sulfonic acid) salt of (+)-(S)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone [that is, (+)-(S)-3-{ 2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin- 10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone-(S)-2-oxo-10-bornanesulfonate (1:2)], from which the base is liberated by treatment with aqueous sodium hydroxide. The first crystallizate is obtained in a purity of about 84% and in a yield of 23.3% based on the racemate used (that is, 46.6% of theory). αD =+9.5° (chloroform; c =1%).

Workup

  1. additionAfter the addition of 5 ml
  2. waitto stand for an additional 2 hours
  3. additiontreated with 3 ml
  4. waitThe solution is now left
  5. waitto stand at room temperature for 85 hours
  6. customThe precipitate obtained
  7. customis subsequently removed by filtration
  8. washwashed with acetone

Sources & evidence

ORD record
ord-97bb6197bf9c457cbc678ee390f09720
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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