Ammonia → HCID 86650790, compound

HRID 1893592Notes

Reaction equation

HRID 1893592 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([N:11]([CH3:45])[C:12](=[O:44])[CH2:13][N:14]([C:31]1[CH:36]=[CH:35][C:34]([C:37]3[N:41]=[C:40]([CH3:42])[O:39][N:38]=3)=[CH:33][C:32]=1[CH3:43])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH3:23])=[O:17])[CH2:6]2.FC(F)(F)C(O)=O.N.[ClH:54].C(OCC)(=O)C>ClCCl.C(OCC)(=O)C.C(OCC)C>[ClH:54].[ClH:54].[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([N:11]([CH3:45])[C:12](=[O:44])[CH2:13][N:14]([C:31]1[CH:36]=[CH:35][C:34]([C:37]3[N:41]=[C:40]([CH3:42])[O:39][N:38]=3)=[CH:33][C:32]=1[CH3:43])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][NH:21][CH2:22][CH3:23])=[O:17])[CH2:6]2

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 86650791HCID 86650791, compound

Product 1

HCID 86650790HCID 86650790, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (753 mg, 1.21 mmol) obtained in step A was dissolved in dichloromethane (2 ml), trifluoroacetic acid (2 ml) was added at room temperature, and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added aqueous ammonia, and the organic layer was extracted 55 twice with dichloromethane. The organic layer was dried over sodium sulfate, the insoluble material was filtered off, and the solution was concentrated under reduced pressure to give a pale-yellow oil. This oil was dissolved in ethyl acetate (2 ml), and 4N hydrochloric acid-ethyl acetate solution (0.75 ml, 3.0 mmol) was added at room temperature. Then, diethyl ether (20 ml) was added to allow precipitation of a solid. This was filtered, washed with diethyl ether, and dried under reduced pressure to give the title compound (655 mg, yield 91%) as a pale-yellow solid.

Workup

  1. extractionthe organic layer was extracted 55 twice with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe solution was concentrated under reduced pressure
  5. customto give a pale-yellow oil
  6. customprecipitation of a solid
  7. filtrationThis was filtered
  8. washwashed with diethyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b0fca7c470a485a81e974d93032eeb1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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