Triethylamine → HCID 68512798, compound

HRID 2041992Notes

Reaction equation

HRID 2041992 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:18])[CH2:13][CH2:14][C:15](O)=[O:16])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][S:24]([NH2:27])(=[O:26])=[O:25].C(N(CC)CC)C.CC1C=CC=C([N+]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O>C(#N)C.CN(C)C1C=CN=CC=1>[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([NH:27][S:24]([CH3:23])(=[O:26])=[O:25])=[O:16])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 252425434-(3-(2-Tert-butylphenoxy)azetidin-1-yl)-4-oxobutanoic acid

Product 1

HCID 68512798HCID 68512798, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-[3-(2-tert-butylphenoxy)azetidin-1-yl]-4-oxobutanoic acid (610 mg, 2.00 mmol), methanesulfonamide (200 mg, 2.10 mmol) and triethylamine (0.84 ml, 6.00 mmol) in acetonitrile (5.0 mL) was added 2-methyl-6-nitrobenzoic anhydride (883 mg, 2.56 mmol) and N,N-dimethylpyridin-4-amine (244 mg, 2.00 mmol) at room temperature. After 16 h, the reaction mixture was partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 10:90 hexane/ethyl acetate) to provide 4-[3-(2-tert-butylphenoxy)azetidin-1-yl]-N-(methylsulfonyl)-4-oxobutanamide (628 mg, 82%) as a colorless solid.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. customseparated
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 10:90 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-95add87034f148c2b00c8b67bb6e108d
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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