Benzoyl isothiocyanate → HCID 89823284, compound

HRID 1619004Notes

Reaction equation

HRID 1619004 reaction equation
[NH2:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH:6]([CH2:7][OH:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:23]([N:31]=[C:32]=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:23]([NH:31][C:32]([NH:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH:6]([CH2:7][OH:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1)=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86697913HCID 86697913, compound

Product 1

HCID 89823284HCID 89823284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To three separate reaction vessels, each containing racemic tert-butyl 3-amino-3-(2-fluorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate (0.142 g, 4.58 mmol) and tetrahydrofuran (18 mL), is added benzoyl isothiocyanate (0.784 g, 4.80 mmol). The solutions are stirred at 22° C., and stirred for 15 hours. The solvent is removed under a stream of nitrogen, the residues combined, and concentrated to provide the crude title compound, which is used without further purification. ES/MS (m/e): 474 (M+H).

Workup

  1. customTo three separate
  2. customreaction vessels
  3. stirringstirred for 15 hours
  4. customThe solvent is removed under a stream of nitrogen
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c55003d338674ceeab4f1752a0cfc02f
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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