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 372167ノート

反応式

HRID 372167 の反応式
[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

参加物

4

反応物 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

生成物 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収率 23.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒3 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-97bb6197bf9c457cbc678ee390f09720
出典データセット
uspto-grants-1978_05
特許番号
US04089861

反応ノート

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