Diisopropylethylamine → HCID 69927875, Verbindung

HRID 1386638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386638
[C:1]([N:8]([CH3:28])[C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[C:30]1([C:36]2([CH2:40][NH2:41])[CH2:39][CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[N:8]([C@H:9]([C:25](=[O:26])[NH:41][CH2:40][C:36]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][CH2:38][CH2:39]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[CH3:28])([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7010604Boc-N-Me-Tyr(Bzl)-OHHCID 22717871(1-Phenylcyclobutyl)methylamine HCl

Produkt 1

HCID 69927875HCID 69927875, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of Boc-NMe-Tyr(OBn)-OH (0.90 g, 2.3 mmol) and C-(1-phenyl-cyclobutyl)-methylamine hydrochloride (synthesized according to the method in Bridges, A. J., Hamilton, H. W., Moos, W. H., Szotek, D. L., N6-substituted Adenosines, U.S. Pat. No. 4,755,594) (0.46 g, 2.3 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (0.97 g, 5.6 mmol) in methylene chloride (10 mL) was treated with DIEA (0.86 mL, 5.1 mmol). The suspension was stirred at room temperature overnight. The resulting solution was concentrated. The residue was taken up in ethyl acetate. The solution was washed with 0.5 M HCl, saturated NaHCO3, dried over MgSO4, filtered, and concentrated. The oil was chromatographed (CH2Cl2:CH3OH 50:1) to give the desired product (1.07 g, 2.02 mmol; 87% yield). MS-APCI 529 (m+1).

Aufarbeitung

  1. customsynthesized
  2. concentrationThe resulting solution was concentrated
  3. washThe solution was washed with 0.5 M HCl, saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe oil was chromatographed (CH2Cl2:CH3OH 50:1)

Quellen und Nachweise

ORD-Eintrag
ord-a2370162c2ac42e8a3bf6720de56b2d7
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265382B1

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