Lithium Hydroxide → HCID 58897144, compound

HRID 1993601Notes

Reaction equation

HRID 1993601 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:27][C:28]([NH:30]C(=O)OCC2C=CC=CC=2)=[S:29])([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[Li+].[OH-]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:27][C:28]([NH2:30])=[S:29])([C:16]2[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=[C:18]([F:26])[CH:17]=2)[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86612964HCID 86612964, compound

Product 1

HCID 58897144HCID 58897144, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To benzyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamothioylcarbamate (269 mg, 0.483 mmol) in Methanol/THF (2 mL/2 mL) was added LiOH (2M, 483 mL, 0.966 mmol). The reaction was refluxed for 40 minutes. The solvents were removed and the residue dissolved in EtOAc. The resulting solution was washed with H2O, brine, dried over MgSO4 and concentrated. The crude mixture was purified by silica gel ISCO chromatography (12 g column) using hexanes/EtOAc (0-50% over 18 min) to give 1-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)thiourea as a pale yellow foam (169 mg, 78% yield). LCMS: 3.8 min [M+1] 454.2 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) δ ppm 5.62 (s, 3H), 6.71 (d, J=7.34 Hz, 3H), 7.11 (d, J=8.56 Hz, 6H), 7.32 (s, 2H), 7.50-7.57 (m, 1H), 7.69 (dd, J=8.56, 2.20 Hz, 1H), 8.28 (s, 1H), 8.64 (s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 40 minutes
  2. customThe solvents were removed
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe resulting solution was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel ISCO chromatography (12 g column)
  8. customhexanes/EtOAc (0-50% over 18 min)

Sources & evidence

ORD record
ord-569be0cafcbd42d1b48e54089ba58ef9
Source dataset
uspto-grants-2010_01
Patent number
US07652023B2

Reaction notes

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