Acetonitrile → HCID 178526510, compound

HRID 1666103Notes

Reaction equation

HRID 1666103 reaction equation
C([Si]([O:8][CH2:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[N:19]=[C:20]=S)(C)C)(C)(C)C.[F-].C([N+:27]([CH2:36][CH2:37][CH2:38][CH3:39])(CCCC)CCCC)CCC.Cl.CN(C)[CH2:43][CH2:44][CH2:45]N=C=NCC.[C:52](#N)[CH3:53]>C(OCC)(=O)C.O>[C@H:36]1([NH:27][C:20]2[O:8][CH2:9][C:10]3[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=3[N:19]=2)[C:37]2[C:38](=[CH:39][CH:43]=[CH:44][CH:45]=2)[CH2:53][CH2:52]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 86639788Tert-butyl-(2-isothiocyanato-6-nitro-benzyloxy)-dimethyl-silane2×

Product 1

HCID 178526510HCID 178526510, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of tert-butyl-(2-isothiocyanato-6-nitro-benzyloxy)-dimethyl -silane (intermediate 2) (3.0 g, 9.0 mmol) in acetonitrile (45 mL) at 23° C. was added R-(−)-1-aminoindane (1.24 g, 9.0 mmol) and the mixture was stirred at 23° C. for 45 min. Added tetrabutylammonium fluoride (1M in tetrahydrofurane, 9.25 mL, 9.0 mmol) and stirred at 23° C. for 1 h. Added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (2.71 g, 14 mmol) and refluxed for 4.5 h. Cooled to room temperature, diluted with ethyl acetate and water, added little 1 M NaH2PO4.2H2O solution to achieve pH 4, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow foam, which was recrystallized from dichloromethane and diisopropylether to give the title compound as a yellow solid (1.94 g, 68%), MS (ISP) m/e=310.4 [(M+H)+].

Workup

  1. temperatureCooled to room temperature
  2. customseparated phases
  3. washwashed organic layer with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent in vacuum
  6. waitleft a yellow foam, which
  7. customwas recrystallized from dichloromethane and diisopropylether

Sources & evidence

ORD record
ord-435a02e51873499faa25c21ecf5db81e
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

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