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 372168Notes

Reaction equation

HRID 372168 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-oxazolidinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The foregoing precedure is repeated using 100 g. of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl }-2-oxazolidinone, 113.2 g. of (+)-camphor-10-sulfonic acid monohydrate and 300 ml. of acetone. The stirring under reflux is carried out for 24 hours in place of 72 hours, and the drying under reduced pressure is prolonged. Whereupon, 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; αD =+14.9°, α364 =+104.0° (chloroform; c = 3.0%); melting point 174°-175° C. (after recrystallization from acetone).

Workup

  1. temperatureThe stirring under reflux

Sources & evidence

ORD record
ord-1f071dae79a643d4b53193af2e4f5211
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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