Benzoyl isothiocyanate → HCID 86697909, compound

HRID 338096Notes

Reaction equation

HRID 338096 reaction equation
[CH3:1][Si:2]([CH3:27])([CH3:26])[C:3]1[S:4][C:5]([C:8]23[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[CH2:13][C@@H:12]2[CH2:11][O:10][NH:9]3)=[CH:6][N:7]=1.[C:28]([N:36]=[C:37]=[S:38])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[C:28]([NH:36][C:37]([N:9]1[C:8]2([C:5]3[S:4][C:3]([Si:2]([CH3:27])([CH3:26])[CH3:1])=[N:7][CH:6]=3)[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:13][CH:12]2[CH2:11][O:10]1)=[S:38])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanate2×HCID 86697910HCID 86697910, compound

Product 1

HCID 86697909HCID 86697909, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl (3aS)-6a-(2-trimethylsilylthiazol-5-yl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (0.218 g, 0.54 mmol) in THF (3.60 mL) is added benzoyl isothiocyanate (0.088 g, 0.54 mmol). The mixture is stirred for 1 hour at room temperature and more benzoyl isothiocyanate (0.044 g, 0.27 mmol) is added. The reaction is stirred for 3 hours at room temperature, concentrated under reduced pressure, and purified by silica gel chromatography eluting with a gradient of 5% to 100% ethyl acetate in hexanes to give title compound (0.204 g, 67%). ES/MS (m/e): 404 (M+H).

Workup

  1. stirringThe reaction is stirred for 3 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. custompurified by silica gel chromatography
  4. washeluting with a gradient of 5% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8f41854dd4d9449bbdf36c2f22cf56c9
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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