Hydrochloric Acid → HCID 23627688, Verbindung

HRID 1171908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171908
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH:35][CH2:36][C:37](O)=[O:38])(OC(C)(C)C)=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[ClH:73]>CN(C=O)C.O1CCOCC1>[ClH:73].[NH2:35][CH2:36][C:37]([N:13]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9][C@@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:38]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Produkt 1

HCID 23627688HCID 23627688, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) and BOC-glycine (35 mg, 0.2 mmol) in DMF (1.0 mL) at room temperature was treated with diisopropylethylamine (35 μL, 0.2 mmol) followed by HATU (84 mg, 0.22 mmol). The reaction mixture was stirred for 2 h then partitioned between EtOAc (10 mL) and a saturated aqueous NaHCO3 solution (10 mL). The organic component was isolated and further washed with brine (10 mL) then dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 40% EtOAc/hexane as eluant to afford BOC-containing coupled product as a foam (85 mg, 81%). LC/MS 7.46 min, [M+1]+ 524. The BOC-protected intermediate was dissolved in a 4 N solution of hydrogen chloride in dioxane and stirred for 2 h then evaporated to a solid which was filtered and washed with diethyl ether to afford product as a colorless solid (42 mg, 49% based on trihydrochloride salt). LC/MS 4.66 min, [M+1]+ 424.

Aufarbeitung

  1. customthen partitioned between EtOAc (10 mL)
  2. customThe organic component was isolated
  3. washfurther washed with brine (10 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas purified by silica gel flash chromatography with 40% EtOAc/hexane as eluant
  8. customto afford BOC-
  9. additioncontaining
  10. customLC/MS 7.46 min, [M+1]+ 524
  11. stirringstirred for 2 h
  12. customthen evaporated to a solid which
  13. filtrationwas filtered
  14. washwashed with diethyl ether
  15. customto afford product as a colorless solid (42 mg, 49% based on trihydrochloride salt)
  16. customLC/MS 4.66 min, [M+1]+ 424

Quellen und Nachweise

ORD-Eintrag
ord-ac55e42d0af643c790d8d4c7ceacbea0
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829713B2

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