Acetic Acid → HCID 53935668, compound

HRID 2185777Notes

Reaction equation

HRID 2185777 reaction equation
[F:1][C:2]([CH3:33])([CH3:32])[CH2:3][CH2:4][C@H:5]1[C:9](=[O:10])[O:8][C@H:7]([C@@H:11]([NH:19][C:20]([C:22]2[CH:31]=[N:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1.C(O)(=O)C.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCOCC1.O>[CH2:12]([C@H:11]([NH:19][C:20]([C:22]1[CH:31]=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21])[C@@H:7]([OH:8])[CH2:6][C@H:5]([C:9](=[O:10])[NH:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:4][CH2:3][C:2]([F:1])([CH3:32])[CH3:33])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7504BenzylamineHCID 57271532HCID 57271532, compound

Product 1

HCID 53935668HCID 53935668, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from Method E (0.10 g, 0.22 mmol) in dioxane (2 mL) was added glacial acetic acid (0.038 mL, 0.66 mmol) and benzylamine (approx. 1 mL, excess). The resulting solution was warmed to reflux for 1 hour, cooled to ambient temperature and diluted with water. The solution was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate (MgSO4), filtered and concentrated. Chromatography on silica gel, followed by recrystallization from methylene chloride/hexanes gave the title compound (0.068 g, 56%). m.p. 183-184° C.

Workup

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux for 1 hour
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialthe combined organics were dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatography on silica gel, followed by recrystallization from methylene chloride/hexanes

Sources & evidence

ORD record
ord-91f212f21469405080af9e6dd776aaad
Source dataset
uspto-grants-2002_06
Patent number
US06403587B1

Reaction notes

Loading…