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

HRID 372170Notes

Reaction equation

HRID 372170 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.[C:33]12([CH2:43][S:44]([OH:47])(=[O:46])=[O:45])[C:40]([CH3:42])([CH3:41])[CH:37]([CH2:38][CH2:39]1)[CH2:36][C:34]2=[O:35].FC1C=CC2SC3C=CC(C)=CC=3C[C@H](N3CCN(CCN4CCOC4=O)CC3)C=2C=1.O=C1CC2C(C)(C)[C@@]1(CS([O-])(=O)=O)CC2>C(C(C)=O)C>[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[CH2:18][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.[O:35]=[C:34]1[CH2:36][CH:37]2[C:40]([CH3:42])([CH3:41])[C@@:33]1([CH2:43][S:44]([O-:47])(=[O:45])=[O:46])[CH2:39][CH2:38]2

Participants

5

Reactant 3

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 monohydrateHCID 86735712(+)-3-[2-{4-[(S)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone (S)-2-oxo-10-bornanesulfonate

Product 1

HCID 86735711(+)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone (S)-2-oxo-10-bornanesulfonate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

10 G. of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone are maintained at reflux with stirring together with 11.3 g. of (+)-camphor-10-sulfonic acid monohydrate [α546 = +28.0° (water; c = 10%)] and 130 ml. of methyl ethyl ketone and the mixture is preferably seeded with a small amount of (+)-3-[2-{4-[(S)-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). An additional 70 ml. of methyl ethyl ketone are added after 3 hours. The mixture is maintained at reflux with stirring for 20 hours. The precipitate obtained is removed by filtration, washed with methyl ethyl ketone and dried under reduced pressure, and there is obtained white (+)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}- 2-oxazolidinone-(S)-2-oxo-10-bornanesulfonate (1:2); αD = +14.1°; α365 = +102° (chloroform; c = 3.0%); melting point 164°-166° C.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture is maintained
  3. temperatureat reflux
  4. stirringwith stirring for 20 hours
  5. customThe precipitate obtained
  6. customis removed by filtration
  7. washwashed with methyl ethyl ketone
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-d8bf16b854964855911e127960065b1b
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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