4-(4-fluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one → HCID 178458806、化合物

HRID 2116638ノート

反応式

HRID 2116638 の反応式
FC1C=CC(C2C3C(=CC([S:18][C:19]4[S:20][C:21]([C:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][CH3:26])=[CH:22][N:23]=4)=CC=3)OC(=O)C=2)=CC=1>CCO.CCCCCC>[F:30][C:27]([F:28])([F:29])[C:24]([C:21]1[S:20][C:19]([SH:18])=[N:23][CH:22]=1)([OH:31])[CH2:25][CH3:26]

参加物

3

反応物 1

HCID 112370004-(4-fluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one

生成物 1

HCID 178458806HCID 178458806、化合物

試薬・触媒・溶媒 1

HCID 21879635Ethanol hexane溶媒

実験手順

A solution of (±)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol (1.2 g) from step 2 of example 1 in EtOH/hexane (20 ml, 1:4) was injected (1×1.2 g) onto a CHIRALPAK AD preparative (5 cm×50 cm) HPLC column (eluting with hexane/EtOH, 4:1; at 75 ml/min with UV detection at 280 nm). The enantiomers were separated with the faster eluting enantiomer having a retention time of ˜19 min (enantiomer #1, (2S)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol) and the slower eluting enantiomer having a retention time of ˜34 min (enantiomer #2, (2R)-1,1,1-trifluoro-2-2-mercapto-1,3-thiazol-5-yl)butan-2-ol). The eluants were concentrated to provide enantiomer #1 (0.468 g, 99% ee) and enantiomer #2 (0.426 g, 98% ee).

後処理

  1. washonto a CHIRALPAK AD preparative (5 cm×50 cm) HPLC column (eluting with hexane/EtOH, 4:1; at 75 ml/min with UV detection at 280 nm)
  2. customThe enantiomers were separated with the
  3. washfaster eluting enantiomer
  4. washthe slower eluting enantiomer
  5. concentrationThe eluants were concentrated
  6. customto provide enantiomer #1 (0.468 g, 99% ee) and enantiomer #2 (0.426 g, 98% ee)

出典と根拠

ORDレコード
ord-5353a990c7b7466e8b1e3c63df33fe77
出典データセット
uspto-grants-2008_10
特許番号
US07439260B2

反応ノート

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