Benzoyl isothiocyanate → HCID 76656263, compound

HRID 2060795Notes

Reaction equation

HRID 2060795 reaction equation
[NH2:1][C:2]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Br:17])[CH:11]=2)[CH:6]([CH2:7][OH:8])[CH2:5][CH:4]([OH:9])[CH2:3]1.[C:18]([N:26]=[C:27]=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[Br:17][C:12]1[CH:11]=[C:10]([C:2]2([NH:1][C:27]([NH:26][C:18](=[O:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[S:28])[CH2:3][CH:4]([OH:9])[CH2:5][CH:6]2[CH2:7][OH:8])[CH:15]=[CH:14][C:13]=1[F:16]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 66852569HCID 66852569, compound

Product 1

HCID 76656263HCID 76656263, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic (1RS,3SR,4RS)-3-amino-3-(3-bromo-4-fluorophenyl)-4-(hydroxymethyl)cyclopentanol (0.48 g, 1.58 mmol) in THF (6.31 mL) is added benzoyl isothiocyanate (0.263 g, 1.58 mmol) and the mixture is stirred at room temperature for 1.5 h. The solvent is removed under reduced pressure and the crude product is purified by silica gel chromatography, eluting with a linear gradient of 0% to 10% methanol in dichloromethane over 20 minutes to give the title compound as racemic mixture (0.602 g, 76%). ES/MS m/e (79Br/81Br) 467, 469 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude product is purified by silica gel chromatography
  3. washeluting with a linear gradient of 0% to 10% methanol in dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-15e50b8487204d42bbfb27afa8f3bdbf
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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