[4-(4-Oxo-piperidin-1-yl)-phenyl]-acetic acid → (4-{4-[2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-phenyl)-acetic acid

HRID 1794815Notes

Reaction equation

HRID 1794815 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:18][CH2:19][C@@H:20]([C:22]1[CH:23]=[CH:24][C:25]([OH:33])=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=1)[OH:21]>>[OH:21][C@H:20]([C:22]1[CH:23]=[CH:24][C:25]([OH:33])=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=1)[CH2:19][NH:18][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 10657278[4-(4-Oxo-piperidin-1-yl)-phenyl]-acetic acidHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 10718924(4-{4-[2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-phenyl)-acetic acid

Procedure

The title compound was prepared from [4-(4-oxo-piperidin-1-yl)-phenyl]-acetic acid (which was obtained in Example 149) and N-[5-(2-amino-(1R)-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 179 as a pale yellowish solid; mp>140° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.25–1.40 (m, 2 H), 1.75–1.95 (m, 2 H), 2.50–3.60 (m, 7 H), 2.88 (s, 3 H), 3.16 (s, 2 H), 4.47 (dd, J=8.0, 4.1 Hz, 1 H), 6.78 (d, J=8.2 Hz, 1 H), 6.84 (d, J=8.3 Hz, 2 H), 6.95 (dd, J=8.2, 1.7 Hz, 1 H), 7.05 (d, J=8.3 Hz, 2 H), 7.16 (d, J=1.7 Hz, 1 H); MS (ES) m/z: 464.1 (MH+); HRMS Calcd. for C22H28N3O6S(M−H)−: 462.1704. Found: 462.1696.

Sources & evidence

ORD record
ord-2fa1df6d066747a381cafe7e78a72b52
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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