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

HRID 2116638Notes

Reaction equation

HRID 2116638 reaction equation
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]

Participants

3

Reactant 1

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

Product 1

HCID 178458806HCID 178458806, compound

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5353a990c7b7466e8b1e3c63df33fe77
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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