Benzoyl isothiocyanate → HCID 86697915, compound

HRID 1619005Notes

Reaction equation

HRID 1619005 reaction equation
[NH2:1][C:2]1([C:16]2[S:17][CH:18]=[C:19]([Br:21])[CH:20]=2)[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:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:22]([NH:30][C:31]([NH:1][C:2]1([C:16]2[S:17][CH:18]=[C:19]([Br:21])[CH:20]=2)[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:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86697916HCID 86697916, compound

Product 1

HCID 86697915HCID 86697915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-amino-3-(4-bromo-2-thienyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate (8.5 g, 22.5 mmol) in tetrahydrofuran (100 mL) at 0° C. is added benzoyl isothiocyanate (3.24 mL, 24 mmol). The resulting solution is warmed to room temperature, and stirred under nitrogen at room temperature for 2 hours. The solution is concentrated and the residue is purified by silica gel flash chromatography eluting with hexanes/ethyl acetate (gradient from 100:0 to 0:100 over 30 min) to give the title compound. ES/MS (m/e): (79Br/81Br) 538/540 (M+H).

Workup

  1. concentrationThe solution is concentrated
  2. customthe residue is purified by silica gel flash chromatography
  3. washeluting with hexanes/ethyl acetate (gradient from 100:0 to 0:100 over 30 min)

Sources & evidence

ORD record
ord-73f63593d0314f4783584c029e8726ac
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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