Sodium Bicarbonate → HCID 69689005, compound

HRID 2120397Notes

Reaction equation

HRID 2120397 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]([CH:8]([CH2:37][CH2:38][C:39]([OH:42])([CH3:41])[CH3:40])[CH2:9][CH:10]([O:33][C:34](=[O:36])[CH3:35])[CH:11]([NH:20][C:21]([C:23]1[CH:32]=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1)=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=O.C([O-])(=O)C.[NH4+:49].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[F:19][C:15]1[CH:14]=[C:13]([CH2:12][CH:11]([CH:10]([O:33][C:34](=[O:36])[CH3:35])[CH2:9][CH:8]([C:6]2[NH:5][CH:4]=[CH:3][N:49]=2)[CH2:37][CH2:38][C:39]([OH:42])([CH3:40])[CH3:41])[NH:20][C:21]([C:23]2[CH:32]=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[O:22])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 69688847HCID 69688847, compound

Product 1

HCID 69689005HCID 69689005, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of acetic acid 3-(2,2-dimethoxy-ethylcarbamoyl)-1-{2-(3-fluoro-phenyl)-1-[(quinoxaline-2-carbonyl)-amino]-ethyl}-6-hydroxy-6-methyl-heptyl ester (150 mg, 0.245 mmol) in acetic acid (2 mL) was added ammonium acetate (1.5 g 19.5 mmol). The resulting mixture was heated to 115° C. for 3 hours, cooled to ambient temperature and diluted with ethyl acetate. The solution was then neutralized with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated. Chromatography on silica gel gave the title compound (22.5 mg, 17%).

Workup

  1. temperaturecooled to ambient temperature
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38fb0aded6bd4e679456afd8c40243fb
Source dataset
uspto-grants-2004_02
Patent number
US06689886B2

Reaction notes

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