Ethylamine hydrochloride → HCID 59577173, compound

HRID 2041990Notes

Reaction equation

HRID 2041990 reaction equation
[C:1]([C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:16])[C:13](O)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([NH2:25])[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C>[C:1]([C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:16])[C:13]([NH:25][CH2:23][CH3:24])=[O:14])[CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 595771001-Azetidineacetic acid, 3-[2-(1,1-dimethylethyl)-4-fluorophenoxy]-α-oxo-

Product 1

HCID 59577173HCID 59577173, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of [3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl](oxo)acetic acid (0.27 g, 0.93 mmol) and ethylamine hydrochloride (89 mg, 1.1 mmol) in acetonitrile (20.0 mL) were added EDCI (0.21 g, 1.1 mmol) and HOBt (0.17 g, 1.1 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure, the resulting residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with 10% sodium bicarbonate, saturated sodium chloride, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 66:34 to 34:66 hexane/ethyl acetate) to provide 2-[3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl]-N-ethyl-2-oxoacetamide (0.14 g, 48%) as a white powder.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. customseparated
  4. washThe organic layer was washed with 10% sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (silica gel, 66:34 to 34:66 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-73831e93e69046b6b2ddd94cb2c0fbb3
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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