Triethylamine → (2R,4S)-5-Biphenyl-4-yl-2-methyl-4-(1H-tetrazol-5-ylcarbamoyl)-pentanoic acid ethyl ester

HRID 1469629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469629
Cl.[CH2:2]([O:4][C:5](=[O:24])[C@H:6]([CH3:23])[CH2:7][C@H:8](N)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH3:3].Cl.C(O[C:29](=[O:49])[C@@H](C)CC(N)CC1C=CC(C2C=CC=C(Cl)C=2)=CC=1)C.CC[N:52](CC)CC.CN(C(O[N:65]1[N:73]=[N:72]C2C=CC=[N:71][C:66]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[Pd].CN(C=O)C.C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:24])[C@H:6]([CH3:23])[CH2:7][C@H:8]([C:29](=[O:49])[NH:71][C:66]1[NH:52][N:72]=[N:73][N:65]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH3:3]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25017086(2R,4S)-4-amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochlorideHCID 67505771HCID 67505771, Verbindung

Produkt 1

HCID 178472550(2R,4S)-5-Biphenyl-4-yl-2-methyl-4-(1H-tetrazol-5-ylcarbamoyl)-pentanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared using similar procedure described in Example 52-1 with appropriate intermediates and conditions. Intermediate 1 and benzyl-H-tetrazole-5-carbonyl chloride (prepared according to J. Med. Chem. 1986, 29, 538-549) are used instead of intermediates 31 and 32. For coupling reaction, Et3N and DCM are used instead of HATU and DMF. For deprotection, hydrogeneation with Pd on carbon is used instead of TFA.

Aufarbeitung

  1. customPrepared

Quellen und Nachweise

ORD-Eintrag
ord-91a384849d6342a18903e1f4ff5a1853
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006249B2

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