Potassium sodium tartarate → 5-(4-Chlorophenyl)-2-({1-[1-(2-chlorophenyl)-2-hydroxyethyl]-1H-1,2,3-triazol-4-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714715Notes

Reaction equation

HRID 714715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH:17]=[C:16]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[N:15]=[N:14]1)[C:9](OC)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([C:21]2[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:28])([F:29])[F:30])[C:23](=[O:24])[N:19]([CH2:18][C:16]3[N:15]=[N:14][N:13]([CH:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH2:9][OH:10])[CH:17]=3)[N:20]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 69940161Methyl (2-chlorophenyl)[4-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,3-triazol-1-yl]acetate

Product 1

HCID 674067985-(4-Chlorophenyl)-2-({1-[1-(2-chlorophenyl)-2-hydroxyethyl]-1H-1,2,3-triazol-4-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

48 mg (0.084 mmol) of the compound from Example 103 were dissolved in 2 ml of THF, and 88 μl (0.088 mmol) of a 1 M solution of lithium aluminum hydride in THF were added at −10° C. After the addition had ended, the mixture was stirred at RT for 1 h. For work-up, 2 ml of saturated aqueous sodium potassium tartrate solution were added at RT, and the mixture was extracted with 5 ml of ethyl acetate. The organic phase was washed once with 5 ml of saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 8 mg (18% of theory) of the target compound.

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with 5 ml of ethyl acetate
  3. washThe organic phase was washed once with 5 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-7125d7eef5ea4f7b93cc3e4442e8d7a9
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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