Sodium Chloride → HCID 90052647, compound

HRID 2284738Notes

Reaction equation

HRID 2284738 reaction equation
[NH2:1][CH2:2][C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])C.[Cl-].[Na+]>CC(C)=O.O.C(OC(Cl)=O)C1C=CC=CC=1>[CH2:27]([O:26][C:23]([NH:1][CH2:2][C:3]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1)=[O:25])[C:28]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 71744123tert-Butyl [4-(aminomethyl)oxan-4-yl]carbamate

Product 1

HCID 90052647HCID 90052647, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 10387Benzyl chloroformateSolvent

Procedure

To a suspension of tert-butyl (4-(aminomethyl)tetrahydro-2H-pyran-4-yl)carbamate (G15, 195 mg) and sodium carbonate (449 mg) in acetone (5 mL) and water (2 mL), benzyloxycarbonyl chloride (241 μL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium chloride were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (4-(((benzyloxycarbonyl)amino)methyl)tetrahydro-2H-pyran-4-yl)carbamate (G16, 141 mg).

Workup

  1. additionwas added at room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-bf071efed71e43a492203c2b221a301f
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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