Trimethylsilyl isocyanate → HCID 66975736, compound

HRID 1022538Notes

Reaction equation

HRID 1022538 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.C[Si]([N:29]=[C:30]=[O:31])(C)C>C1COCC1>[C:30]([NH:1][CH2:2][CH:3]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1)(=[O:31])[NH2:29]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 66975023HCID 66975023, compound

Product 1

HCID 66975736HCID 66975736, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6RS,7SR)-6-(aminomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (125 mg) in THF (1.5 mL) was added trimethylsilyl isocyanate (57.7 mg), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (160 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe diluted solution was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ee02e4c089a0421f99fda829818c9a69
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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