Sodium Bicarbonate → HCID 69689005, compound

HRID 1266649Notes

Reaction equation

HRID 1266649 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-d758f4d1b6334e5cba4a997b0f12f228
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

Loading…