Sodium Bicarbonate → HCID 178442445, compound

HRID 425423Notes

Reaction equation

HRID 425423 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]([CH3:44])([CH2:42][CH3:43])[CH2:8][C:9](=O)[CH2:10][NH:11][C:12](=O)[C:13]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)=[CH:18][CH:17]=1)[CH3:14].C(=O)(O)[O-].[Na+]>>[CH2:32]([O:31][C:30](=[O:39])[NH:29][C:13]([C:12]1[NH:11][CH:10]=[C:9]([CH2:8][C:7]([CH3:6])([CH3:44])[CH2:42][CH3:43])[N:5]=1)([CH3:14])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)=[CH:18][CH:17]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 86637808HCID 86637808, compound

Product 1

HCID 178442445HCID 178442445, compound

Conditions

Temperature
160 °C

Procedure

Ammonium acetate (2.53 g, 32.79 mmol) was added to an ambient temperature solution of benzyl {2-[(4,4-dimethyl-2-oxohexyl)amino]-1-[4-(5-fluoropyridin-2-yl)benzyl]-1-methyl-2-oxoethyl}carbamate (350 mg, 0.66 mmol) in xylenes (minimal volume). After stirring in a sealed tube at 160° C. for 1 hr, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated. 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: 515.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. 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-a8ef7ed87d5a42d1b7b5f06d8a99611b
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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