HCID 131729363, compound → HCID 131729362, compound

HRID 420272Notes

Reaction equation

HRID 420272 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([CH2:27][C@H:28]([OH:33])[C:29]([F:32])([F:31])[F:30])[C:24]([N:34]=CN(C)C)=[C:23]([F:39])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:40])([CH3:4])([CH3:3])[CH3:2]>CCO.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+].[Cl-].[Cl-].[Zn+2]>[NH2:34][C:24]1[C:25]([CH2:27][C@H:28]([OH:33])[C:29]([F:31])([F:32])[F:30])=[CH:26][C:21]([CH2:20][C@H:13]2[C@H:12]3[C@@H:17]([N:9]([CH2:8][C:7]4[CH:41]=[CH:42][CH:43]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=4)[C:10](=[O:40])[O:11]3)[CH2:16][S:15](=[O:19])(=[O:18])[CH2:14]2)=[CH:22][C:23]=1[F:39]

Participants

6

Reactant 1

HCID 131729363HCID 131729363, compound

Product 1

HCID 131729362HCID 131729362, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of N′-[4-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-6-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-phenyl]-N,N-dimethyl-formamidine (0.11 g, 0.17 mmol) in anhydrous EtOH (3 mL) was added ZnCl2 (0.12 g, 0.86 mmol) and the reaction mixture was heated at reflux for 8 h. The reaction mixture was diluted with EtOAc and aq. K2CO3 solution. The product was extracted with EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated. The crude product was purified by flash-chromatography on silica gel (hexane-EtOAc 2:1 to 1:2) to yield the title compound as a colorless foam: TLC (hexane-EtOAc 1:1) Rf=0.39; HPLC RtA=2.21 min; ESIMS [M+H]+=573.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 8 h
  3. extractionThe product was extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash-chromatography on silica gel (hexane-EtOAc 2:1 to 1:2)

Sources & evidence

ORD record
ord-1a6eceb668be4a27946635e457efe9a1
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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