Ammonium Acetate → HCID 178442425, compound

HRID 1881503Notes

Reaction equation

HRID 1881503 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]([CH3:37])([CH2:35][CH3:36])[CH2:8][C:9](=O)[CH2:10][NH:11][C:12]([C:14]1([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=3)=[CH:23][CH:22]=2)[CH2:18][CH2:17][C:16](=[O:19])[NH:15]1)=O>>[CH3:6][C:7]([CH3:37])([CH2:35][CH3:36])[CH2:8][C:9]1[N:5]=[C:12]([C:14]2([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][N:28]=4)=[CH:23][CH:22]=3)[NH:15][C:16](=[O:19])[CH2:17][CH2:18]2)[NH:11][CH:10]=1

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 66705623HCID 66705623, compound

Product 1

HCID 178442425HCID 178442425, compound

Conditions

Temperature
160 °C

Procedure

Ammonium acetate (1.18 g, 15.4 mmol) was added to an ambient temperature solution of N-(4,4-dimethyl-2-oxohexyl)-2-[4-(5-fluoropyridin-2-yl)benzyl]-5-oxopyrrolidine-2-carboxamide in xylenes (minimal volume). After stirring in a sealed tube at 160° C. for 1 hr, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. High pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid afforded the title compound. (M+H) found: 421.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. washHigh pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid

Sources & evidence

ORD record
ord-0aad72d772414a2389a48431840d4561
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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