(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 86584567, compound

HRID 1794822Notes

Reaction equation

HRID 1794822 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C@@H:27]([C:29]1[CH:30]=[CH:31][C:32]([OH:40])=[C:33]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:34]=1)[OH:28]>>[CH2:1]([O:8][NH:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([NH:25][CH2:26][C@H:27]([OH:28])[C:29]3[CH:30]=[CH:31][C:32]([OH:40])=[C:33]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:34]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 22220228HCID 22220228, compound

Product 1

HCID 86584567HCID 86584567, compound

Procedure

The title compound was prepared from N-benzyloxy-4-(4-oxo-piperidin-1-yl)-benzamide (which was obtained in Example 155) 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>70° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.2–1.40 (m, 2 H), 1.70–1.90 (m, 2 H), 2.50–2.95 (m, 5 H), 2.92 (s, 3 H), 3.70–3.85 (m, 2 H), 4.47 (dd, J=8.0, 4.2 Hz, 1 H),4.89 (s, 2 H), 6.81 (d, J=8.2 Hz, 1 H), 6.92 (d, J=9.0 Hz, 2 H), 7.00 (dd, J=8.2, 2.0 Hz, 1H), 7.18 (d, J=2.0 Hz, 1 H), 7.30–7.50 (m, 5 H), 7.60 (d, J=9.0 Hz, 2 H); MS (ES) m/z: 555.3 (MH+); HRMS Calcd. for C28H35N4O6S (MH+): 555.2272. Found: 555.2260.

Sources & evidence

ORD record
ord-c50722d642cb4c318fa21468acf20cdb
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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