Ethanol → HCID 59356620, compound

HRID 1260001Notes

Reaction equation

HRID 1260001 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:40][CH:41]([CH3:43])[CH3:42])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:22][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:20]1)=[O:17])C.O.[NH2:46][NH2:47].[CH2:48]([OH:50])[CH3:49]>>[C:48]([NH:46][NH:47][C:4](=[O:3])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:40][CH:41]([CH3:43])[CH3:42])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)=[O:26])[CH2:22][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:20]1)=[O:17])(=[O:50])[CH3:49]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 58355516HCID 58355516, compound

Product 1

HCID 59356620HCID 59356620, compound

Conditions

Temperature
0 °C

Procedure

tert-Butyl (3S,5R)-3-[{[1-(3-ethoxy-3-oxopropyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (307 mg) was dissolved in ethanol (10 ml), hydrazine monohydrate (243 μl) was added and the mixture was heated under reflux for 6 hr with stirring. The reaction mixture was concentrated, ethyl acetate was added to the residue, and the mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in THF (5 ml), and triethylamine (209 μl) was added. The reaction mixture was cooled to 0° C., acetic anhydride (71 μl) was added dropwise and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object product (292 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washthe mixture was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionThe residue was dissolved in THF (5 ml)
  9. additiontriethylamine (209 μl) was added
  10. additionacetic anhydride (71 μl) was added dropwise
  11. stirringthe mixture was stirred at room temperature for 15 hr
  12. additionThe reaction mixture was diluted with aqueous sodium bicarbonate
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0170fc3f69af450ab09fdd2cfaf95a27
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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