Pyridine → N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide

HRID 1445762Notes

Reaction equation

HRID 1445762 reaction equation
[C:1](OC(=O)C)(=O)C.N1C=CC=CC=1.[CH2:14]([O:21][CH2:22][CH2:23][CH:24]([NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=1[F:37])[C:25]([OH:27])=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][CH2:22][CH2:23][CH:24]([NH:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=1[F:37])[C:25](=[O:27])[CH3:1])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 589514334-Benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid2×

Product 1

HCID 58951463N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide

Conditions

Temperature
90 °C

Procedure

Add acetic anhydride (0.97 mmol) and pyridine (0.58 mmol) to a round bottom flask containing 4-benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid (1.0 mmol) (See Intermediate 35) and heat to 90° C. for two hours. After this time, remove the heat and concentrate in vacuo. Wash crude with 1N hydrochloric acid and water while extracting with diethyl ether. Concentrate the organics in vacuo and purify on an Isco CombiFlash® chromatography system eluting with ethyl acetate and hexane. MS (m/e) (79Br/81Br): 408.3/410.3 (M+1)

Workup

  1. customAfter this time, remove the
  2. temperatureheat
  3. concentrationconcentrate in vacuo
  4. washWash crude with 1N hydrochloric acid and water
  5. extractionwhile extracting with diethyl ether
  6. concentrationConcentrate the organics in vacuo
  7. custompurify on an Isco CombiFlash® chromatography system
  8. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-8a6c132dd22447289cb3cd365b804427
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…