(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → Diethyl(2S)-2-[(4-{4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]pentanedioate

HRID 1794823

Reaktionsgleichung

Reaktionsgleichung von HRID 1794823
[CH2:1]([O:3][C:4](=[O:29])[C@@H:5]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[NH2:30][CH2:31][C@@H:32]([C:34]1[CH:35]=[CH:36][C:37]([OH:45])=[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:39]=1)[OH:33]>>[OH:33][C@H:32]([C:34]1[CH:35]=[CH:36][C:37]([OH:45])=[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:39]=1)[CH2:31][NH:30][CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([NH:13][C@@H:5]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:3][CH2:1][CH3:2])=[O:29])=[O:28])=[CH:16][CH:17]=2)[CH2:22][CH2:23]1

Komponenten

3

Edukt 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69654880(2S)-2-[4-(4-Oxo-piperidin-1-yl)-benzoylamino]-pentanedioic acid diethyl ester

Produkt 1

HCID 69654677Diethyl(2S)-2-[(4-{4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]pentanedioate

Versuchsvorschrift

The title compound was prepared from (2S)-2-[4-(4-oxo-piperidin-1-yl)-benzoylamino]-pentanedioic acid diethyl ester (which was obtained in Example 157) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 180 as a white solid; mp>75° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.18 (t, J=7.1 Hz, 3 H), 1.19 (t, J=7.1 Hz, 3 H), 1.20–1.45 (m, 2 H), 1.80–2.10 (m, 4 H), 2.41 (t, J=7.4 Hz, 2 H), 2.50–2.95 (m, 5 H), 2.93 (s, 3 H), 3.75–3.85 (m, 2 H), 4.05 (q, J=7.1 Hz, 2 H), 4.10 (q, J=7.1 Hz, 2 H), 4.35–4.45 (m, 1 H), 4.45–4.55 (m, 1 H), 6.82 (d, J=8.3 Hz, 1 H), 6.94 (d, J=8.9 Hz, 2 H), 7.01 (dd, J=8.3, 2.0 Hz, 1 H), 7.18 (d, J=2.0 Hz, 1 H), 7.74 (d, J=8.9 Hz, 2 H), 8.38 (d, J=7.5 Hz, 1 H); MS (ES) m/z: 635.1 (MH+); HRMS Calcd. for C30H43N4O9S (MH+): 635.2745. Found: 635.2735.

Quellen und Nachweise

ORD-Eintrag
ord-416dfea2efca4a8db4d8a00d0d89590c
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022716B2

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