Triethylamine → HCID 69904971, Verbindung

HRID 841138

Reaktionsgleichung

Reaktionsgleichung von HRID 841138
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:16]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[C@H:17]([C:43](O)=[O:44])[CH2:18][C:19]1[N:23]=[CH:22][N:21]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(#N)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][N:6]([C:43](=[O:44])[C@@H:17]([NH:16][C:46]([O:48][CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)=[O:47])[CH2:18][C:19]1[N:23]=[CH:22][N:21]([C:24]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:20]=1)[CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14845245Methyl 3-((2-(tert-butoxy)-2-oxoethyl)amino)propanoateHCID 15545280Z-His(Trt)-OH

Produkt 1

HCID 69904971HCID 69904971, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the compound from Step 1 (0.434 g, 2 mmol) in methylene chloride (10 mL) was added Cbz-His(Trt)-OH (1.062 g, 2 mmol), triethylamine (0.8 mL, 5.7 mmol) and HBTU (0.758 g, 2 mmol) dissolved in acetonitrile (10 mL). The reaction mixture was stirred overnight at room temperature. The solution was concentrated, the residue taken up in ethyl acetate and washed three times with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. Chromatography was carried out on silica gel, using 30% hexanes in ethyl acetate as eluent, to give an oil; 1.38 g (94% yield). MS-APCI: M+1=732.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. washwashed three times with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-7b8cf208f08d49fab90c7b5c1af1990d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369034B1

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