2,4,6-Trimethylpyridine → 3-{[5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic Acid Tert-butyl Ester

HRID 1061716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061716
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]1[S:19][C:18]([C:20]([OH:22])=O)=[CH:17][CH:16]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][C:28](=[O:38])[CH2:29][CH:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:26])([CH3:25])[CH3:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC(C)=CC=1C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[C:23]([O:27][C:28](=[O:38])[CH2:29][CH:30]([NH:37][C:20]([C:18]1[S:19][C:15]([C:13](=[O:14])[NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:16][CH:17]=1)=[O:22])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Komponenten

7

Edukt 4

HCID 79532,4,6-TrimethylpyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14557402Tert-butyl 3-amino-3-phenylpropanoateHCID 222852255-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carboxylic Acid

Produkt 1

HCID 540767673-{[5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic Acid Tert-butyl EsterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

With continued reference to Scheme G, 5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carboxylic acid (200 mg, 0.704 mmol) was reacted with 3-Amino-3-phenyl-propionic acid tert-butyl ester (187 mg, 0.845 mmol) in 4.0 ml of anhydrous DMF using HATU (321 mg, 0.845 mmol) with 2,4,6-collidine (0.25 ml, 2.112 mmol), chromatographied on silica gel using ethyl acetate: hexane (8:2) to give 200 mg (58% yield) of the desired product as a clear semi-solid oil. 1H NMR (400 Mhz, CDCl3) 1.3 (s, 9H), 1.45 (s, 9H), 1.7 (m, 2H), 2.9 (ddd, 2H), 3.25 (m, 2H), 3.5 (q, 2H), 4.85 (bs, 1H), 5.55 (m, 1H), 7.23 (m, 1H), 7.33 (m, 4H), 7.4-7.6 (m, 4H).

Quellen und Nachweise

ORD-Eintrag
ord-e4ff4c47a8334334a6bbf207a556f226
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960594B2

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