L-Tartaric acid → 3-[2-{4-[(R)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone (R,R)-tartrate

HRID 372169Notes

Reaction equation

HRID 372169 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.[C:32]([OH:41])(=[O:40])[C@@H:33]([C@H:35]([C:37]([OH:39])=[O:38])[OH:36])[OH:34]>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.[C:37]([C@@H:35]([C@H:33]([C:32]([O-:41])=[O:40])[OH:34])[OH:36])([O-:39])=[O:38]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 30425092-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)-

Product 1

HCID 1317111013-[2-{4-[(R)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone (R,R)-tartrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.0 G. of the salt of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone with (+)-(R,R)-tartaric acid [α546 =+15.0° (water; c = 10%)] in the molar ratio of 1:1 are dissolved in 500 ml. of acetone and, after stirring for 24 hours at room temperature, the mixture is filtered. The filter cake is washed with acetone, dried under reduced pressure, and there is obtained 3-[2-{4-[(R)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone-(R,R)-tartrate (1:1); α365 =+98.6° (dimethylformamide; c = 2.0%); decomposition point 172° C. After liberation of the base by treatment with aqueous sodium hydroxide, there is obtained crystalline (R)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone; α365 =+183.85° (chloroform; c = 0.5%) in a purity above 99%. The yield amounts to 54.4% of theory.

Workup

  1. filtrationthe mixture is filtered
  2. washThe filter cake is washed with acetone
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-8fc2ca35d40c4dd184a8db12f32ee6bd
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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