Benzoyl isothiocyanate → HCID 54558117, compound

HRID 363513Notes

Reaction equation

HRID 363513 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][C:11]1[S:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][C:11]1[S:12][C:13]([NH:16][C:31]([NH:30][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[S:32])=[CH:14][CH:15]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 54044708HCID 54044708, compound

Product 1

HCID 54558117HCID 54558117, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Ethyl N-(tert-butoxycarbonyl)-3-(5-amino-2-thienyl)-DL-alaninate (4.21 g, 13.4 mmol) in acetone (75 ml) at 0° C. was added benzoyl isothiocyanate (2.55 g 15.6 mmol). The mixture was stirred for 5 minutes at 0° C., warmed to room temperature and stirred for 2 hours. The solvent was removed at reduced pressure and the resulting oil dissolved in ethyl acetate, washed with 1N aqueous hydrochloric acid, brine and dried over magnesium sulphate. The solvent was removed at reduced pressure to give a dark green viscous oil. The crude product was purified by chromatography on silica gel eluting with 1:3 ethyl acetate/hexane to yield Ethyl N-(tert-butoxycarbonyl)-3-(5-(3-benzoylthioureido)-2-thienyl)-DL-alaninate (4.91 g, 77%) as a yellow solid.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 hours
  3. customThe solvent was removed at reduced pressure
  4. dissolutionthe resulting oil dissolved in ethyl acetate
  5. washwashed with 1N aqueous hydrochloric acid, brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed at reduced pressure
  8. customto give a dark green viscous oil
  9. customThe crude product was purified by chromatography on silica gel eluting with 1:3 ethyl acetate/hexane

Sources & evidence

ORD record
ord-bb4815f4036e4493b009bf3fd2b01ba9
Source dataset
uspto-grants-1999_02
Patent number
US05874472

Reaction notes

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