Water → HCID 86670027, compound

HRID 450490Notes

Reaction equation

HRID 450490 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[C:20]([O:23][CH2:24][C:25](Cl)=[O:26])(=[O:22])[CH3:21].O>C1COCC1>[C:20]([O:23][CH2:24][C:25]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:12])=[O:26])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 86670027HCID 86670027, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(3-aminopropyl)carbamate (1.00 g, 5.74 mmol) in THF (10 mL) were added triethylamine (1.6 mL, 11.5 mmol) and acetoxyacetyl chloride (0.678 mL, 6.31 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water (30 mL), and the mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined and washed with brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→1:4) to give the title compound (1.35 g, 86%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 mL×3)
  2. washwashed with brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→1:4)

Sources & evidence

ORD record
ord-a853379a581344cb82a8bfb3164b568b
Source dataset
uspto-grants-2013_07
Patent number
US08486965B2

Reaction notes

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