Cyclopropylamine → HCID 47451248, compound

HRID 2423055Notes

Reaction equation

HRID 2423055 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.[NH:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:16](O)=[O:17]>ClCCl>[C:22]([O:21][C:19](=[O:20])[NH:14][CH2:15][C:16](=[O:17])[NH:13][CH:10]1[CH2:12][CH2:11]1)([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531Diisopropylethylamine

Product 1

HCID 47451248HCID 47451248, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

—TBTU (5.1 g, 16.5 mmol), DIPEA (2.9 ml, 16.5 mmol) and cyclopropylamine (2.2 ml, 33 mmol) were added to a solution of BOC-Gly-OH (2.63 g, 15 mmol) in dry dichloromethane (10 ml). After 17 h stirring, the reaction mixture was concentrated under reduced pressure and water was added to the residue. The product was extracted into ethyl acetate. The combined organic phases were washed with an aqueous solution of 2M hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, brine, dried over sodium sulfate and concentrated under reduced pressure to give 2-cyclopropylcarbamoylmethyl-carbamic acid tert-butyl ester (847 mg). The product was used in the following step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe product was extracted into ethyl acetate
  4. washThe combined organic phases were washed with an aqueous solution of 2M hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, brine, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2f3d877b9fe438eba9ea663ceeacbf3
Source dataset
uspto-grants-2011_06
Patent number
US07960560B2

Reaction notes

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