Methyl valinate hydrochloride → (S)-3-Methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl ester

HRID 75776

Reaktionsgleichung

Reaktionsgleichung von HRID 75776
[C:1]1([NH:7][C:8](=[O:24])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21](O)=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:26][O:27][C:28](=[O:34])[C@@H:29]([NH2:33])[CH:30]([CH3:32])[CH3:31].[K+].[Br-]>>[CH3:26][O:27][C:28](=[O:34])[C@@H:29]([NH:33][C:21]([C:19]1[O:18][N:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:24])=[CH:15][CH:14]=2)[CH:20]=1)=[O:22])[CH:30]([CH3:32])[CH3:31]

Komponenten

4

Edukt 3

HCID 111190Methyl valinate hydrochlorideHCID 253877Potassium BromideHCID 673550113-[4-(3-Phenyl-ureido)-phenyl]-isoxazole-5-carboxylic acid

Produkt 1

HCID 46181355(S)-3-Methyl-2-({3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-butyric acid methyl esterAusbeute 65 %

Versuchsvorschrift

The title compound was prepared from 3-[4-(3-phenyl-ureido)-phenyl]-isoxazole-5-carboxylic acid and (S)-2-amino-3-methyl-butyric acid methyl ester hydrochloride as set forth in Example 5 and was obtained in 65% yield. Mass (ES+): 437 (M++1); IR (KBr): 3342, 3262, 1743; 1665, 1598, 1550; 1H NMR (DMSO-d6) δ: 0.92 (2×d, 6H), 2.18 (m, 1H), 3.63 (s, 3H), 4.27 (t, 1H), 6.94 (t, 1H), 7.25 (t, 2H), 7.42 (d, 2H), 7.58 (d, 2H), 7.64 (s, 1H), 7.80 (d, 2H), 8.72 (s, 1H), 8.92 (s, 1H), 9.14 (d, 1H).

Aufarbeitung

  1. customwas obtained in 65% yield

Quellen und Nachweise

ORD-Eintrag
ord-1678d693759e46348a8632f4e02fc08f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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